Sissy Finishing School

Tag: anal training

  • Anal Stretching For Sissy Sluts

    Anal Stretching For Sissy Sluts

    Interested In Anal Stretching ?

    Anal Stretching Assignment For Sissies
    Time For Your Anal Stretching Class Sissies

    Anal stretching is something that most sissies becoming interested with at one point or another.  It is a very common fetish.  Anal stretchingcan be a small amount or an extreme amount of stretching.  Sometimes people are a bit scared to start the anal stretching process, but it is a very enjoyable feeling when done the correct way!

    Gathering Your Anal Stretching Supplies

    The first thing you will want to do is gather your supplies.  You will want at least 3 differently sized objects or toys; A small, medium and large.  The sizes used during anal stretching will vary based on your own personal experience.  You will also want lots of lube!   Lube is really important for a pleasurable anal stretching experience.

    Time For Anal Stretching

    Once you have everything, it’s time to get started!  You will want to start by lubing up your smallest toy really good.  Then it’s time for you to insert that toy into your ass nice and slow; It’s best to take it inch by inch.  Try hard to focus on relaxing your muscles so that you can take your toy in completely.  Once you have taken the smallest toy completely in your ass, you will relax for a few minutes letting your ass adjust to the size.

    After you have adjusted to the smallest toy, you will slowly move the toy in and out of your ass, being careful to not overstimulate yourself.  If you feel your arousal beginning to peak you will stop and let yourself cool down before fucking yourself some more.

    Now it is time to move onto the medium sized toy where you will perform the same actions as you did with the small toy.  You may take longer to adjust to the medium sized toy so it may be best to wear it for a bit longer before trying to fuck yourself with it.

    Try wearing the toy under panties while you check emails or make dinner.  Once you have completely adjusted to the medium toy you may fuck yourself nice and slow, letting your body fully adjust. Again be careful to not overstimulate yourself, there is one more size to go!

    Time For The BIG Anal Stretch

    Once you are completely relaxed and ready it is time to try out the biggest toy that you have! You will want to you a copious amount of lube with this toy and really take your time as you slowly start to insert it.  This part of anal stretching may bring a small amount of pain and that is okay.

    Be sure to listen to your body though!  If you work slowly inch by inch, letting your body take the toy slowly into your ass you should be just fine!  Soon you will be able to take every inch of your biggest toy thanks to anal stretching.

    Ms Lily and I have years of anal stretching experience!  Don’t be shy, give us a call and let’s get you started on a anal stretching assignment tailored just for you !

    Until later……
    Ms Isabelle

  • Anal Training Fun

    Anal Training Fun

    Anal Training Toy
    Anal Training Toy

    For this anal training assignment you will need several toys in varying sizes. If you have access to butt plugs, you will need a small, medium and large plug for this training exercise. If you do not have access to butt plugs then find some items from around your house (i.e. candlestick, hairbrush, cucumber).

     

     

    If you are a regular to anal training then make sure you are using bigger plugs for each part of the anal training segment. You may also want a rubber glove if you prefer for the warm-up portion of this anal training exercise. Last but not least, you will need copious amounts of lube.

     

    Warm-up Anal Training

    First you are to get into a comfortable position where you can reach back to your tight ass. If you want to wear a rubber glove for this part, put it on now. You will then cover your fingers in lube. Then you will massage your asshole slowly, inching one fingertip into your asshole, spreading the lube around. You will then start to sink you finger deeper and deeper into your ass, probing it gently as you lube up your tight hole. Once you have gotten use to the feeling of your finger, pull it out and re-apply a generous amount of lube to TWO fingers. You will then slowly and gently press those 2 lubed fingers to your tight hole, stretching it open as you press deeper and deeper.

     

    For at least 3-5 minutes you will alternate between fucking your asshole with two fingers and stroking your prostate by curving your fingers toward your prostate while they are inserted deeply inside yous ass.

     

    Once you are adequately stretched out and aroused it is time to move on to the first toy.

     

    Part 1: Smallest Toy For Anal Training

     

    You will start by lubing up the smallest of the toys that you have collected, making sure that it is slippery wet. Then you will squat down on the tip of your toy, feeling it stretch your ass open just a bit. Now slowly lower yourself onto that toy, letting it stretch open your ass as you take more and more of it. Once you have taken as much of the toy in your ass as possible, sit back to hold it in nice and deeply before slowly stroking your cock. Focus on the feelings of arousal as they surge through you body with each stroke; Focus on the feeling of the toy deep inside of you ass, possibly even touching your prostate.

     

    Now bounce up and down just slightly, moving the toy only a few inches in and out at first. Spend 2-3 minutes bouncing on your toy in this fashion before you bounce up and down harder and faster. You should be sliding that toy all the way in and out now, really getting lost in the feelings of being fucked by this toy and slowly stroking your hard dick. Spend another 3-5 minutes fucking yourself in this fashion to open up your ass nice and wide for your next toy.

     

    Part 2: Medium Toy For Anal Training

     

    For the medium toy, you will follow the same instructions as the smallest toy. The only modification is that you will spend 3-5 minutes fucking yourself slowly and gently before you move on to the faster, more thorough fucking. Once you have really started to fuck your medium toy nice and hard, you are to spend 5-8 minutes fucking yourself in this fashion to ensure that you are loose enough for the large toy.

     

    Before you move onto the biggest toy, you will lube up several fingers on both hands and gently use your fingers the literally stretch your ass as much as possible. Remember a little pain is normal, but do not push yourself to hard.

     

    Part 3: Largest Toy For Anal Training

     

    Now take the largest toy and lube it up really good, making sure that it is super slippery and wet for your ass. You will position yourself over the toy and slowly lower yourself onto it, inch by inch. If the stretching becomes to much at any point, stop and wait for 1-2 minutes before proceeding to take more and more of the toy.

     

    Once you have taken in as much of the toy as you can, you are to rest there for a full 2 minutes while you jerk and stroke your cock for me. After your resting period, you will start to slowly fuck the toy inch by inch, being careful to keep as much of the toy in you as possible for the next 5 – 8 minutes.

     

    As your arousal peaks, you will start to fuck the toy much more aggressively. You will fuck it hard, fast and taking it in and out as much as possible for the next 5-8 minutes while you jerk your cock at the same time. You should be bouncing on your toy hungrily till you cum all over the place. Now, clean up your cum with your tongue if you are adventurous and let me know in the comment section how much fun you had with my anal training assignment.

    Until later…….

    Ms Isabelle