Hello Mistresses hope you are all doing well. So this sissy has a slight confession before she joined this site she would have never thought about doing anything more than some slight fingering in the shower so this sissy wants to thank you for giving her that little push she has needed to experience another level of submission and pleasure.

Well this assignment starts a few days ago in the shower when sissy was cleaning herself she decide to touch that oh so naughty place ;D and for some reason felt extra sexy when she did so this sparked a curiosity inside her and she knew just where to get the information that she needed. After looking at the anal submission assignment this sissy decided to go all out she bought a anal starter kit, lube, and went to the sort to purchase a douche. Once home she decided to try out the douche and to be honest this was kind of scary remember this sissy has only played using her finger and maybe up to the second knuckle so when she saw that it was a good 4 inches or so long and about as big around as her middle finger sissy was nervous. But this sissy had her mind set and she started by stretching out her hole as much as she could with her fingers while in the shower letting the warm water help relax her and once she was able to fit two fingers in with relative ease she got out her douche. So now this sissy fills the douche with warm water (any other girls reading this make sure its not to hot or cold) and lubed up the shaft (giggle) with lots of lube, with care and patients she slowly pushed the tip in and with her recent research she pushes against the tip like she is having a bowl movement. This action helped pop the tip in and once past the ring it easily slid in all 4 inches and it felt really weird at first but not bad. So now this sissy squeezes the ball slowly and can feel the warm water enter her its a strange sensation that she can only describe as a slight glowing inside her, after she has emptied the ball she slowly pulls out the douche and wow a jolt of pleasure shoots threw her as last little bit leaves her pussy. Sissy then looks down and notices that she has a string of precum leaking out of her clitty so she does what every good sissy should do and scoops it up and licks it off her fingers mmm so good. Now she makes her way over to the toilet and expels the liquid witch feels very strange but again not unpleasant. This sissy then repeats the process two more times to get as clean as she can and for some practice, she will do this every two days until her special days comes up on the weekend.

So now that this sissy is clean for the week she decides to do some edging to prepare for this weekend. First she starts off with some slight touching around her pussy just some rubbing and a little pressure, this starts to make her hard so she rubs her clitty with just her thumb and finger mmmm god this feels so good to sissy. Now that sissy is good and hard and plenty of lube on her finger she starts to insert the tip in just a bit and then pulls out a little then back in again each time going just a little bit further all the while still stroking her clitty ever so gently, this sissy has found that a gentle touch on her clitty is much more pleasurable than the fast rough motion she was used to. After a few moments of slow probing she is able to fit two fingers in pushes in just above the second knuckle she feels a great pressure in her welling up and precum is now easily flowing out of her clitty. In and out she fingers herself while rubbing her clitty and just as she could feel the pressure building up her muscles starting to tense she slows down and eventually removes her fingers (she knows better than to cum on her non special days) and cleans up her precum off the sheets and her legs. This sissy does this once more before her kit arrives and her special day.

So now the moment sissy has been waiting for she has imagined what it would be like to use her first toy for a week now and she is very excited so first let sissy tell you what she will be using. So first she has a three inch plug with a 3/4 inch base a 4 inch plug with a 1 inch base and a prostate massager. This sissy starts off with the small plug first as she inserts it into her pussy she is already getting hard and with a slow constant push she finally feels the plug pop in as the biggest part passes her ring. She instantly feels her clitty leaking and a sense of girlish femininity washes over her as she sits down and wiggles her tush on the bed pushing it even deeper. As this sissy sits there she feels her nipples as they are now rock hard and with one had on her clitty the other on her nipple she imagines that the plug is a hard cock in her pussy (sissy is getting hard just writing this) slowly rubbing herself for what seems like an eternity she starts to feel herself cum and stops. With heavy breathing sissy then takes out the small plug and gets the other ready this one is a bit longer and bigger but since sissy is already stretched out a bit the plug goes in with minimal effort but the pleasure is much greater. For the first time sissy feels her prostate being touches and it sends a storm of sensation down her clitty the surprise and shock of it actually causes her to let out a squeak. Sissy then lets her pussy get used to the plug and then slowly pulls it out and then pushes it back this the ultimate pleasure for sissy as she has fantasized about having a cock in her pussy for sometime now and she feels so feminine just imagining a Master or Mistress controlling her dominating her she is no longer a man but a sissy who is destine to be a future cock whore. Now here is when sissy got a little adventurous while sissy was playing with herself her roommate came back home so sissy decided to leave the plug in pull up her panties and put on a pair of shorts she then walks out into the kitchen right past her roommate and bent down to get a bottle of water out of the fridge. Just knowing that she had the plug in and her roommate had no idea was so exciting she was having a hard time hiding her hard clitty oh god I wished to be his sissy maid right there and then and have him bend me over the counter. So now sissy is back in her room harder than she has ever been still feeling the plug stretching her wider and every now and then hitting her prostate sits back down on her bed and starts to rub her clitty and nipples again it does not take long before she explodes into an amazing orgasm. This sissy jerked and twitched as she let out a weeks worth of pent up sexual frustration the afterglow was amazing and the feeling of a plug in her pussy made her feel so girlish so submissive it was amazing. But we are not done yet sissy still has one more toy to play with 😀 so after about a half hour (plug still in her pussy) of recovering this sissy got out her prostate massager. Now this thing did not come with dimensions but it was a lot bigger than inch. Sissy then removed her plug and after lubing up the prostate massager started to insert it, sissy was glad she left that plug in because it was so big it took so much concentration to relax then push then relax over and over again little by little getting it in then finally the head passes sissy’s ring and it slides home almost pulling out of her had and immediately hits her prostate. This was not like the plug where it just barely touch it no this was pressing up against it with such pressure sissy let out a moan she is sure her roommate heard it was like someone was rubbing sissy from inside her clitty and she had the overwhelming feeling like she had to pee and a tingling sensation starting deep within radiating out. So now sissy lays down on her side just feeling it push against her she notice that just her breathing caused the toy to move and stimulate her prostate its was amazing, sissy could feel the precum being pushed out of her clitty and starts to massage it with just her finger and thumb. This went on for I don’t even know how long until sissy came it was not like a jerking tense orgasm but one that welled up from inside it felt warm like little electric shocks and it was so satisfying its the first time that this sissy has felt complete after she has pleasured herself she really does not know how to describe it. After a bout 15 minutes or so sissy was finally able to get up and take the toy out she then decided to put a plug back in and kept it there for the rest of the night, now sissy uses a plug most nights she is home and will be trying to work her way up to larger plugs in the future.

This sissy is now hooked on playing with her pussy and she thanks the House for giving her that little push she needed. The experience showed sissy how great it can feel to give up control to let something inside your most vulnerable part of yourself and just let all fear and worry fade away sissy truly felt feminine and girlish as she can only imagine how it would feel as a women lets a man penetrate deep in her. Sissy will definitely be spending her special days with something deep in her pussy for now on.

With love
submissive sissy taylor