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IttyBittySissy

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About IttyBittySissy

  • Birthday 10/31/1995

Member Info

  • Briefly Describe your last sexual encounter:
    Male and Female. Slight bondage and sadistic play. Anal for both parties.
  • My Favorite Toy
    Honestly .. my 7” cyberskin dildo or my 9” blue jelly dildo. They feel so good, every. single. time.
  • About Me
    A freaky male with a Dom side and a Sissy side. Play with me however you like, so long as you fit my interests (;
  • Location
    Colorado
  • # of sex toys you own?
    10-30
  • Marital status
    Single
  • What is your age & gender?
    I am a 23 year old male.

Profile Information

  • Interests
    Females-21 to 50/Dominatrix/ Traps/Developed Femboys/Attractive Cross Dressers/Trans Females
  • Location
    Colorado
  • Gender
    Male

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IttyBittySissy's Achievements

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  1. Same! I’ve been exploring anal masturbation for about a year now and I’ve gotten to the point where I can sissygasm 5-25 times a session and just gush and gush 😩 don’t even get me started on actual anal orgasms. They leave me breathless and in a pile of goo, eager for another. Anal orgasms and prostate orgasms from masturbation(I would say sex but I’ve never experienced anything outside of masturbation) are easily the most powerful orgasms. Even if you’re a female and don’t have a prostate. There’s no denying the intense sensation that floods every part of your being when you reach orgasm and then the afterglow feeling that radiates throughout your body. Yikes, I.. I think it’s time for more fun tonight 🤤🙈
  2. Hello my lovelies. 

    My profile doesn’t want to cooperate and share my info so pleasseeee just ask ❤️ 

    I am open to every and all submissions, replies, and posts but please always be respectful and appropriate when necessary. 

  3. Hello Master/Mistress -if you’ve gotten this far you may as well inquire about more. I am the IttyBittySissy I am well trained and always a fun to play with. I’d love to chat and if you get me worked up enough I always love to play with myself. Talk Soon 😘
  4. Hello, and Welcome. -as this is my first post please bare with me. The topic today that I’ve chosen to spill the sploog about is prostate orgasms also known as P-Orgasms. However, I will refer to it as a sissygasm on occasion. If this isn’t your preferred term don’t fret, it isn’t direceted at anyone in particular. A lot of men are afraid to express interest in anal or anything pleasurable about it simply because of societal judgment(at least that’s how it is here in America.) While it’s become more accepted to enjoy same-sex relationships, be identified how we see ourselves, what we enjoy sexually, etc.. we still have a long way to go. Anyways, for those who are slightly unfamiliar with what or where the Prostate actually is or does I have a small lesson for you. The main function of the Prostate is to provide and secrete semen allowing the sperm access to easier travel out of the testicles and through the shaft, eventually exiting the tip of the penis. It is located approximately 1”-3 1/2” inside the male rectum on the frontal wall and feels like a small ball inside you(referred to as a walnut shape). If correct pressure is applied directly at the point the scrotum meets the part between your asshole and scrotum you can feel pressure on the prostate. Now I know this sounds silly, but if your penis is normally smaller when flaccid there’s a better chance you’ll have more successful prostate play. However, if you’re penis is on the bigger side while flaccid you can still have the same amount of success and pleasure! You’ll just have to train your pelvic floor muscles a bit more - better learn how to perform keggle exercises (; When it comes to actual prostate play that’s really up to how used to anal play you are and how willing you are to give into the amazing sensations not only anal can provide but prostate massaging, milking, and full blown Sissygasms can really be. I would start with either using a finger if you enjoy that or a small dildo. Locate where your prostate is so you know exactly what angle to penetrate. Most men prefer pressure to start or a slight rubbing sensation. For me being a bit more experienced I absolutely love a dildo inside my little asshole sliding back and forth about 4” deep. For beginners just worry about the pressure you feel and the sensation at the base of your penis. Two things can happen(whether one or the other or both happen is up to experience, mindset, and your bodies ability to actual achieve Sissygasm) 1. You’ll have our beloved Prostate Orgasm. Usually it’ll start out like you have an intense sensation at the base of your penis. It’ll build and build until you feel a sensation similar to peeing except it’s also coursing through your pelvis and depending on how much you love anal stimulation it can honestly become body numbing. Now as I mentioned befor if your pelvic walls are strong you can squirt A LOT of prostatic fluid, several inches, several times. For some men they never experience the overwhelming uncontrollable gush of a prostate orgasm then there are sissies like me who can have anywhere from 5-25 Prostate orgasms in one masturbation session. It just all depends on your body and your mindset. Next. 2. (My Favorite pleasure ever) The Anal Orgasm The ever elusive yet most powerful orgasm of all. Whether you are male, female, or anything you prefer .. as long as you have an asshole with feeling this will forever be the most intense and fulfilling orgasm IMO (in my opinion) The trick with achieving an anal orgasm is 10000% mindset. Period end of story. If you aren’t fully comitted, open minded, patient, and most of all actually into anal you will most likely never achieve anal orgasms. Now there will be some of you who are all of the above and will still never experience one and while that’s unfortunate, you’ll still be able to have the raw pleasure of anal stimulation and trust me that’s powerful enough. A full blown Anal Orgasm will leave you shaking, breathless, and eager for another. For me an anal orgasm starts at the tip of the dildo inside of me. I have to have my dildo deep inside my asshole pounding at a fast pace, have had at least one sissygasm, or at least an hour into anal masturbation when my rectum is at its most senstitive state. The feeling will start deep inside of me and a warm sensation will start to radiate into my pelvis, lower back, and thighs. I ALWAYS end up squeezing the dildo as I pound it into me making my breathing temporarily stop as every muscle in my body clenches. A powerful electric spark will shoot up my spine sending a warm flooding sensation throughout my body and what I call an “afterglow” feelings tingles in my brain and eventually spreads throughout my body. Now that’s just the first one. If I can have multiple anal orgasms without squirting and having a sissygasm as well my “afterglow” feelings become more and more intense the more I cum like a good anal slut. Honestly, my best advice I can give you is once you feel yourself either hit the edge of having an anal orgasm or start tipping over it GO HARDER. You will thank me later. So many guys hit that wall and stop. KEEP GOING! Push yourself over the edge of normal anal pleasure and ride the amazing pleasure waves once you actually feel an anal orgasm. Position, Toy, and Speed. These will all be completely up to the individual. For me I have to have a toy(usually a dildo no shorter than 6” and at least wider than 1 1/2”. But that started out much smaller than what I use now (was a 4” glass dildo that was 1” thick then complimenting that with a 7” dildo that was 1 1/2” thick. I used to only be able to have a sissygasm while I rode a dildo. Now I can sissygasm in just about any position I want as many times as I want. For achieving anal orgasm I used to only be able to leaned over a bed or couch, and pounding my dildo deep and fast until I exploded in pleasure and I had to keep going. Now I can also have an anal orgasm in any position I want depending on the toy. The last thing I want to talk about is Prostate Milking. While it’s incredibly pleasurable to milk your prostate (usually with just pressure or massaging of the prostate) it also is medically beneficial and also let’s be honest, it’s so sexy to leak fluids uncontrollably. Those are my tips and tricks for Prostate Orgasms and Anal Orgasms. If you have any questions please ask.
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