u/Ambitious-Loss3429

so she was my best friend mom , he was one of my friends but was straight and i already started at that time going slutty , my friends knew i was gay but blurry knowledge , and one of the days , i was at his house waiting for him to get ready to walk to college together since they live near the college , then i firstly see her , she was shorter than me with few centimeters , very hot and thick body , amazing posture and perfect sized boobs , even her leggings were almost see thru so you could see the red panties under them if she bend over and looked innocent ,not the type of dommes that i imagine ,and i was sitting in my boy-shorts , smooth legs and hands of course and even caged , she offered a drink and talked with me a bit she was single at that time btw and she started like slightly flirting with me at first i though just compliments ,but when she asked for my number it got a little bit strange , but cool she said she wanna check for her son cause most of the times he closes his phone , anyway i gave her my number ,and by that he came downstairs and she walked with us to the door saying "it's great pleasure to meet you cutie" and she hugged me with her hands almost on my ass but no groping just gently taping

tbh i got so excited from such thing , that i even came twice while rubbing my caged clitty just from the imagination ,but again she's my friend's mom , so i said maybe she was being nice , till one of days i was in party and wore some short dress and dropped the pics as status, she commented "wow cutie that's hot ,sure you'd be hotter if you try my lingerie" , i acted normal towards such "compliment" and a bit cheeky , but she responded straight forward , "do you wanna get dommed" she texted me saying that in two days her son will travel for a week and she'll have the house for herself and she said "he doesn't have to know about anything" , i was a bit concerned ,but as long as it was casual and for fun as she stated i was ok , so i prepared my self to go on the weekend at night for our date , i went caged & plugged , but luckily i had my key in the necklace around my neck
i knocked and she opened wearing almost a lingerie in a form of a dress and she welcomed me with a hug , but this time she GRABBED my ass and kissed my neck so things were almost ready for anytime , but she offered me some high class wine and sat down close to me on couch started talking about my sissy journey and what are my kinks and she talked about her journey as domme/lesbian woman and that she enjoyed both being fucked and pegging , all that while moving her fingers around my neck till the end of my back , then she took the glass from me and made the first move while feeling my thighs with her hands and moving till she touched my cage , she lift the dress up to find the cage and she laughs about how slutty i am , and out of no where i who went few times with women asked her to suck her titties which was sth of impossible kinks to achieve , she instantly dropped her bra and got my head on her back after taking off all my clothes and taking off my plug and placed my mouth on her titties which surprisingly were lactating so i actually tasted some milk while she was spreading my legs with her hands and my hole with her fingers .

after ten minutes ,she said that's enough cutie time to break you , and took my hand ,walked me upstairs to her room first i thought breaking meant some bdsm things but actually she sth else more than that , she took the key from my necklace and unlocked the cage then she said "get over the bed" and i instantly obeyed her orders and on her wooden made bed she got 2 cuffs tied to each bedpost behind my head and tied each of them to each hand just to fixate me from what's gonna happen , "so you can't fuck a woman with your clitty" she says , and she starts like literally absorbing my limp clit which at that time stopped from being hard for most of the times since two months from then , so she licks and licks and all i do is moaning then licks while fingering just hoping i get partial hard and nothing happens then heavily stroking my clit while sitting on my face as a 69 position and bit by bit my clit gets a bit hard that she notices so she grabs it from its lower end with 3 fingers just to keep hard as possible and gets up from me and says"let's see how much you're going to last" and turns around while holding my semi hard clit and fixate it in its place and slowly goes down with her asshole targeting my clit till touched and just when she starts sitting and pressing on tip of my clit i instantly drop all of my cummies without being in her or anything and a lot of bitches moaning from me , she laughs and says i told you you're such a good girl and get on my face again just to lick her pussy while she started training my ass with her fingers that are dipped in my cummies , then 5 minutes she says "my turn" and turns me with my broken clit between bed and my belly and she gets her strapon and instantly goes inside me i already cam for 2 times one as sissygasm while sucking her titties and being fingered and one of my impootence and limpicity , but at such point i accepted that i should pleasure my new mommy as long as she wants and be her sissy free use for any time , so she went banging me for like half an hour while spanking me and with other hand rubbing her clitty she cam within that period of time and continued till she got horny again so she decided to go creative and turned me again to be on my back while returning plug in my ass and she helped me readjust to be half sitting and she went scissoring me with my small limp red exhausted clit which was comparable to her normal size pussy and she kept going and moaning hard both of us till i see her orgasm shaking while kissing me and saying "thank you cutie" and just like that she unlocked the cuffs and had me sleep with her both of us naked on her bed till next day unluckily most of time after she had her son so we reduced our meetings as much as possible but this specific night was unforgettable

It'd be better if it's self doing tasks cause I'll try all of them since I don't have a partner rn :( , all I know is humping and rubbing that's my peal knowledge in clitty humiliation beside caging , what additional things you can add to the list, doesn't have to be kink only , maybe some mode shrinks your clit instantly once you get in it , what do you think I should try?

So it was 2 years ago , during summer holiday i had this call from one of my best friends inviting me to go hiking with him for the weekend , i was at this point a professional sissy on 5 years of experience , he kinda knew i date men , he was kinda bisexual as i was told later , he was in very great shape for a guy , and i was in a great shape as a sissy girl , but lazy sissy since all i had done so far in this holiday was go work and get home play with myself then sleep , that's it so i thought why not and maybe i could tease him a bit since he was single and hadn't seen dick for 2 months back then so i wore a normal t shirt but on a boyshort with having my cage on and plugged just in case ;)

it was like if it was us only in the forest , some cool views and some cozy vibes , while walking we talked about his past relationships ,how they went , he was kinda frustrated that most girls he knew were not good at giving heads which upsets him , i thought to myself "of course nobody would appreciate such dick as a sissy or femboy would" at this point i could see his dick drawn lines under the shorts which was kinda swimwear it was perfect size for me almost 1.5 of my dildo which i find very fitting and pleasuring me , we found some small waterfall connected to a pure water lake and i found him getting shirt off and jumping in while saying "water is aweesome come in" i got my shirt off and jumped in the water , he said" i'll teach you how to float on your back " and i really missed a touch from a guy so i accepted with no hesitation , at such point if he was blind enough not to see the cage and plug through my tight shorts he got certain that i'm a whore for dick when he was hoding my back on water and then touches my ass as if he's balancing me then he touches the diamond plug and after that his behavior changed bit by bit he almost had me floating touching him standing so my elbow and belly side is feeling his dick as if he was rubbing his dick on me , i got it and decided let's tease him a bit , the day's still long , so i got out of water saying "i got bored of water" let's continue our walk , he got of water with no shame of his 6 inch dick anyone could see .

5 minutes later and we reached the part that started the real tension , it was sandy pyramid-mountain alike shape that consists of some high steps , so no climbing but for each step you going up , you require either having great muscles in your hand or someone pushes you up , of course for him that was a dream , and without even me asking i found him grabbing my ass high as if he wants to push me up , i gave no response cause my clitty was gonna explode from horniness in my cage so i got on upper step and waited for him then next step he lifts me while one hand on my ass cheeks and other groping my tiny caged clit at this point he knows for sure i'm caged and plugged , then for last step he said something i dont even recall cause i thought was gonna sissygasm soo almost in climax point but i found him so close to my back before pushing and also pushing me on the step edge itself so i was kinda squeezed between his body , mostly his dick which i don't even know under the shorts or not at that point and my body from front is touching the edge of last step while cage is hitting this part then he pushes me all the way up from my waist , so all my body is rubbed by his dick and my caged clit rubs the step edge and i think i sissygasmed at this point but no strong pnc hit me

when he got up first thing he said "you want it" , i without hesitation got on my knees like a slut and got my shirt off waiting for him to get it in my mouth , and after all the horniness he built in me i gave him the best blowjob he had as he stated later all in the middle of no where it seems till he holds my head strongly and gladly swallowed it all , and he got on the ground exhausted for five minutes while i rested on my belly shirtless, just rubbing my caged clit against the sandy ground , i used to do such thing on my kitchen floor and fully naked but it was first time i do it in public , 5 minutes and i find a big sound,not hurting spank on my ass and he got up again pulled my hair to get me on my knees for new blowjob , and just when he started precumming he get his dick off from my mouth and gets my shorts off with a smile , and gets me on top of him to do 69 position with him getting off the plug and licking my sweaty hole while spanking my ass and i'm licking his balls and his dick while rubbing my cage on his chest , then 5 minutes and he gets me on pronebone position all my naked body on smooth sand while caged clitty broken between my big thighs so any movement he makes breaks it even more , and at one moment he puts it all in no time or gradual scheme , i moaned very hard that i think anyone around could hear it easily then he goes rough with my useless clit getting roughly rubbed on the smooth sand and me moaning while having my second sissygasm , i find him climaxing with a bit of shaking while he creampies me and i can feel it in my belly almost if it was impregnating me , then he rests on my back for five minutes and says "this is the best day of my life" , and he kisses my cheek while i feel his cum dripping from me and he gets me up and gimmie my clothes to wear and we continued the hicking normally and it went as normal picnic-trip mode and we got to the dorm on 8 pm with two more fucking sessions and we promised it's all casual and tbh that was fair that's the kind of relations i love , and we still best friends:)

so it was 2 years ago , during summer holiday i had this call from one of my best friends inviting me to go hiking with him for the weekend , i was at this point a professional sissy on 5 years of experience , he kinda knew i date men , he was kinda bisexual as i was told later , he was in very great shape for a guy , and i was in a great shape as a sissy girl , but lazy sissy since all i had done so far in this holiday was go work and get home play with myself then sleep , that's it so i thought why not and maybe i could tease him a bit since he was single and hadn't seen dick for 2 months back then so i wore a normal t shirt but on a boyshort with having my cage on and plugged just in case ;)

it was like if it was us only in the forest , some cool views and some cozy vibes , while walking we talked about his past relationships ,how they went , he was kinda frustrated that most girls he knew were not good at giving heads which upsets him , i thought to myself "of course nobody would appreciate such dick as a sissy or femboy would" at this point i could see his dick drawn lines under the shorts which was kinda swimwear it was perfect size for me almost 1.5 of my dildo which i find very fitting and pleasuring me , we found some small waterfall connected to a pure water lake and i found him getting shirt off and jumping in while saying "water is aweesome come in" i got my shirt off and jumped in the water , he said" i'll teach you how to float on your back " and i really missed a touch from a guy so i accepted with no hesitation , at such point if he was blind enough not to see the cage and plug through my tight shorts he got certain that i'm a whore for dick when he was hoding my back on water and then touches my ass as if he's balancing me then he touches the diamond plug and after that his behavior changed bit by bit he almost had me floating touching him standing so my elbow and belly side is feeling his dick as if he was rubbing his dick on me , i got it and decided let's tease him a bit , the day's still long , so i got out of water saying "i got bored of water" let's continue our walk , he got of water with no shame of his 6 inch dick anyone could see .

5 minutes later and we reached the part that started the real tension , it was sandy pyramid-mountain alike shape that consists of some high steps , so no climbing but for each step you going up , you require either having great muscles in your hand or someone pushes you up , of course for him that was a dream , and without even me asking i found him grabbing my ass high as if he wants to push me up , i gave no response cause my clitty was gonna explode from horniness in my cage so i got on upper step and waited for him then next step he lifts me while one hand on my ass cheeks and other groping my tiny caged clit at this point he knows for sure i'm caged and plugged , then for last step he said something i dont even recall cause i thought was gonna sissygasm soo almost in climax point but i found him so close to my back before pushing and also pushing me on the step edge itself so i was kinda squeezed between his body , mostly his dick which i don't even know under the shorts or not at that point and my body from front is touching the edge of last step while cage is hitting this part then he pushes me all the way up from my waist , so all my body is rubbed by his dick and my caged clit rubs the step edge and i think i sissygasmed at this point but no strong pnc hit me

when he got up first thing he said "you want it" , i without hesitation got on my knees like a slut and got my shirt off waiting for him to get it in my mouth , and after all the horniness he built in me i gave him the best blowjob he had as he stated later all in the middle of no where it seems till he holds my head strongly and gladly swallowed it all , and he got on the ground exhausted for five minutes while i rested on my belly shirtless, just rubbing my caged clit against the sandy ground , i used to do such thing on my kitchen floor and fully naked but it was first time i do it in public , 5 minutes and i find a big sound,not hurting spank on my ass and he got up again pulled my hair to get me on my knees for new blowjob , and just when he started precumming he get his dick off from my mouth and gets my shorts off with a smile , and gets me on top of him to do 69 position with him getting off the plug and licking my sweaty hole while spanking my ass and i'm licking his balls and his dick while rubbing my cage on his chest , then 5 minutes and he gets me on pronebone position all my naked body on smooth sand while caged clitty broken between my big thighs so any movement he makes breaks it even more , and at one moment he puts it all in no time or gradual scheme , i moaned very hard that i think anyone around could hear it easily then he goes rough with my useless clit getting roughly rubbed on the smooth sand and me moaning while having my second sissygasm , i find him climaxing with a bit of shaking while he creampies me and i can feel it in my belly almost if it was impregnating me , then he rests on my back for five minutes and says "this is the best day of my life" , and he kisses my cheek while i feel his cum dripping from me and he gets me up and gimmie my clothes to wear and we continued the hicking normally and it went as normal picnic-trip mode and we got to the dorm on 8 pm with two more fucking sessions and we promised it's all casual and tbh that was fair that's the kind of relations i love , and we still best friends:)

so for a currently single sissy , it'll be first time i'll buy a sex toy that's not very cheap relatively like a dildo or a cage , like does loosing control and having the machine itself work on you gives you some glance of being with a partner , if so do you suggest a specific machine you used and liked?

This point is very much about preference but the best position I had for such goal was milking myself in doggy position and having the cell right under me, you can be on three limps while having the 2nd hand milking you or the other way which i prefer one hand milking and the other hand fingering myself and my head is the third part alongside with the knees touching the bed surface just to breathe well the actual part of your head is one of your cheek so you breathe normally i hope you can imagine the position correctly , it's perfect I recommend it for any girl who hasn't tried , it works perfect with some tips for me :lights off , just pure fantasy no type of content I use like audio or videos , full naked , and having a light blanket covering my whole back (light blanket to lighten the burden on your neck) and even sometimes i moan when mood hits , the most important tip is using your weak hand , I've read a lot about this topic which relates body awareness with weaker or less used limbs ,your brain deals with it a lot less of being part of your body so it would feel a little bit of someone's hand is milking you , when using the more used hand your brain and is hundred percent aware of it being your hand and part of your body , the milking i prefer is very slow full hand and don't mind using some more power , if i have time i stop touching myself just before i reach climax and then wait some time just fingering myself till i become limp and repeat this cycle couple of times till i drop cummies while limp , but most of the times to be honest i drop it from first time with out stopping to touch myself but still go slow no need for fast throbbing , you can have however you want but the details I included in this paragraph sends me to heaven feel free to try it .

So about a year ago , i was in my penultimate year of college ,trying to cover my living expenses , room expenses which I became alone in after my roommate went back to his home country as a gap year , as you know he was my very close friend we were in this friends with benefits win win relation , no strings just all friendly and warm , he was the only one knew my sissy side and he paid most of room expenses so i didn't care about work hours that much , but fast forward when he left me i missed him as a friend, and also i had to work more hours just to get basic expenses , and of course i kept in touch with him online I did enough money , but almost studied nothing in that first semester on my own , just did classwork assignments to get any grades , but the main projects was much difficult to do on my own , I started searching for some teams cause i know i can't do it on my own in small time and with such small studying knowledge , i got into some teams for all courses except for two courses. I tried looking for any friend i know but no one enrolled in neither.

I did not know what to do at such point and decided i start studying until i figure it out , through money i made in first month vanished part by part , i had two options back then to quit both courses and make some money on studying time or quit college and be a sissy sex worker "kidding" or ask some strangers i don't know well in both courses for this projects as a favor , so while chatting with my roommate , he suggested i check with some nerdy close friend of him he said he may agree for such thing ,and he'd give him a call but i shall offer him some of my cake cause he's a bit kinky, and we both had a laugh about what i thought was a joke and i decided i'd give it a try maybe the nerd would agree just from knowing his friend referred him to me , so maybe who knows?

I knocked on his room door ,wearing normal some what tight jeans but nothing erotic, he let me in , and we had a talk about semester , our friends and he seemed a bit introvert , somewhat handsome , normal body which i prefer and his room was clean and tidy, and i felt cool around him, he told me he had a gf but they broke up and his now also alone in his room and offered a cup of tea , i said water is fine ,he came to me walking while sitting and having my glass of water and gently moves my head up with his hand on my chin to be in eye to eye contact, saying "i know your financial and courses situation and your problem in projects but if i let you with me as a team member what would you give in return if the project is already finished? , I know you're bisexual ,correct? ", I said yes I didn't even have another response in my head but began to form a thought on what some weird hole i'm falling into, he says "i'm also bisexual and i'll be real honest with you I kinda want a sexual favor from you that's it , and then both of us will never get in contact together even projects are to be submitted without any revision you'll get the grade you want" , I was left speechless starring at him , don't know what to say , he says "i don't want your response now just think of it" and here's the kind of favor i want specifically and he hands me a pink neat paper , says "i want you to read it carefully tonight and decide whether you're into it or not then get back to me and whatever you good or not it was nice knowing you, sweetie;)" i was a bit stunned but decided to get out of his room and see wtf is going to happen then ,tbh i did not feel scared at all he speaked direct and without any lying he stated his purpose so something for something but of course i want to see what's he into

Something that motivated me even more was my sexual frustration , I told you no roommate to pleasure me , no "back then" current boyfriend , closeted sissy in rural area in belgium , so getting into a good warm relation was difficult , additionally i don't have time for such thing , so all i had was my pink diamond plug , pink cute cage and my pink dildo i mount everday during shower or ride while studying , and the schedule i was on to lock myself all week except for thursday to get to relief myself whether from mounting the dildo or with two-finger playing so maybe being horny affected my decision later ,I decided any bdsm stuff would get me to decline his offer no thinking cause that's not my cup of tea ,anyway i get to read the paper and I get a bit stunned but also hard in my cage , you know that kind of excitement where you feel like you small hard clitty would get broken from the cage any sissy tried chastity would get it ;) , the pink paper is divided as 3 parts : program synopsis , which states that i have to spend one day with him and to obey the rules in second part and any breaking of rules leads to repeat the day ,the program targets enslaving me to be as obedient pet whose goal is satisfying and obeying rules and orders i take without refusing and after the end of the day the program is finished and i get what i desire .

coming to the second part which is the rules i got more interested : spend all day on fours , spend all day caged , fully naked , whatever ordered should be done , you can use your hand normally , but only if it's for sissifying tasks or accepted deal from your owner ,like using a fuck machine or turning on some hypno while room-alone, no single word , your orders would be to give a blowjob or moan if ordered to and some other similar orders , anything leaks from you or your owner is to be licked all from the floor , you'll also act as a maid , so some kitchen parts would be in your level in case you're ordered to make some tea or food , but all while on fours , no taking off your collar ,and sleeping on floor, and you're expected to come fully clean , will sleep on floor beside your master and start your day normally according to rules, side note there would be a camera on 1.5 m level viewing all room just in case you break the rules and stand third part included a small message saying : "all done in friendly and kinky play nothing violent , just all role play and we can even decide a safe word if wanted nothing serious we just having fun" , I finished the paper at midnight and i found my self humping my bed with my caged clitty and there's a huge cummies leak circle around my clitty , at this point i knew i liked it , but i decided to give my roommate a late "pretending to be upset" call to be sure he's safe for being around , and my roommate tells me "i told you i knew he's a bit kinky and also he's into sissies but i can ensure he's really not a serial killer he just wants to have some fun". and by that call i decided to go for it , cause i don't wanna to drop the courses and tbh that's not the only reason;).

I get myself ready with my cage with me , and butt plug and dildo ,cause i don't know what he has , and i get my pink bag on with normal clothes and go on about 7 pm knocking on his door he opens and let me in , before he starts talking , i interrupt and say ,ok i agree but after this we don't know each other and i pass both projects , he smiles and says ok we good , he takes the paper and tells me can you sign it with name kelly , i said ok whatever , and tells me gimmie one second and he gives me a blue diamond plug and a pink dildo and fuck machine saying he borrowed the fuck machine and he's gonna return it but i can keep the dildo and plug as a gift he bought for me after the end of the day ,tbh i really got more excited because i never got to try a fuck machine before, then he gives me a pink collar with a rope attached to it written kelly on it , and says "i assume you read the rules you can go to the bathroom and get yourself ready and we'll start at 9 pm " and he gets off all of his clothes saying "see no problem no need to be shy" , I say ok and get a glance on his dick it's good size and the size that's going to pleasure you normally so neither huge which is sth i don't like nor small which is comparable to my dildo which i use daily , so perfect fit. i get undressed in bathroom had a shower ,get the collar around my neck and my own cage on my clit then trained on the mounted on wall dildo of mine and kept it in case get bored then play on my phone while thinking how would this day be , what can happen and then my timer rings and it's 8:55 i get on fours like a good sissy as he wanted , and practice walking on fours while plugged and caged, then at 9 :00 he opens the door found me and says "good girl , see it's gonna be very normal don't worry you might even get bored" i shake my head , cause remember the only sound i can do is moaning , so he grabbed the rope of my collar and walks a bit with me walking around the room then stopped at his desk where he had mounted to its side his blue dildo he says take it in your mouth while i finish some assignment , i start licking it infront of him then he ignores me at all while i keep sucking it for almost half an hour while keeping this doggy posture position of a good girl sucking , then he gets up and looks at my tiny clit leaking a bit on floor and some of my saliva getting on floor from sucking , he says "lick all you leaks till i take a shower and get ready for you", i looked on the floor and saw my leaks and instantly starts licking it all with my stupid clit not even stopping , and get back to sucking the blue dildo , and after 10 minutes ,i hear shower stops and he gets out all naked and he gets the blue dildo and mount it to the fuck machine ,removes my plug, and gets me from my collar in such a position he's sitting on his bed and i'm facing his dick , and the tip of dildo is almost in me waiting to be fully inserted , he says "come on taste it " , and while on my fours i only moved my mouth up and down on his dick and even he tries to hold my head to position it correctly , not deep throating he was super gentle but just position it correctly then starts the fuck machine on low speed , i start feeling it in me while sucking , so the start of my spit roasting , some inner sissy urges starts in me you know that feeling when you're on your way to sissygasm , my moans get's a bit hearable then he gets the machine on higher speed while fixing my head and basically fucking my mouth , my moans and gagging on his dick gets louder with higher urges and feeling , i'm gonna explode from my tiny clitty with a lot of cummies then on highest speed , i can't control myself , full ecstasy and horniness , i can't feel but the cummies on the door of my clitt while he speeds his own fucking speed then while all that happens , i explode first while all on my fours , of course i can't see it because i still blowing him but i can describe it as intense stream of what i saw later to be semi white cummies , and i call it cummies cause even if quantity is big , this is still sissy juice that comes from sissy pleasure while caged and limp and getting penetrated not in a man position but i dropped for like half a minute non stop , and about the feeling , you're basically in heaven , anyone tried sissygasm would agree , anyway i was not in a position to update with my sissygasm and see my cummies on floor until five minutes later when he takes his dick away from my mouth and gets his cum on floor , then he lays on bed and says "you know your duty ,cutie" and then i instantly get to lick all his cum and my cummies not wasting any part of it even the machine was working on medium speed then he says "you get to sleep under me when the machine timer stops" and spanks me a slightly loud spank with his hand that i even leaked more and he turns off the lights , 10 minutes later , the machine stopped , i found a pillow and slept on my belly , my tiny cute clit was even horny i checked it before sleeping but tbh i was low key frustrated that he didn't fuck me himself , then i get to sleep , 2 hours later maybe on 2 am , while i'm fully naked while on my belly , feel his hands on my ass grabbing it , and his mouth kissing my neck and cheeks saying "i told you'd sleep under me " his dick was hard and its length was along all my ass crack plus my tiny clitty which was pointing backwards while my all body was touching the ground , he starts fingering me and telling me no moaning , cute slut , and since it's an order i bite my pillow instead to avoid any repeating , tbh i lowkey during the whole experience wanted a repeat , but he updates the fingering first one finger and revolving around my hole , then in and out then two fingers and all i can do is humping the floor and biting my pillow , then he says "now you're ready" and firstly he adjusts my position instead of my belly is the part touching floor he put my clit under my belly and the remaining area of body still touches the floor , so my clitty is between my belly and floor and most of our weights is on the poor caged clitty movements would break it more (i already had reached the point where i cum limp while 2 finger playing since 2 months from this night so no problem from further breaking) ,then he starts adjusting his dick with his left hand while spanking me and kissing me , and bit by bit he's in me while i'm fixed and just biting my pillow , then he rests for 5 minutes and starting the rough fucking , now my points of pleasure now isn't only my hole but my neck his kissing , my poor clitty which is moving with our weights on it , but luckily the floor was a bit soft not rough to hurt my skin , then he goes faster and faster and i again feel my clitty leaking alot , that's the first time i sissygasm twice a day , and he goes more fast and rough at 2 am while no sound is coming up from me , so the only sound you can hear in the whole dorm his body hitting my red slapped cheeks or his spanks , at this part i'm being used and that's the goal of his program which popped to my mind until 10 minutes later i feel his dick pulsating in me and he kisses my neck says "thanks sweetie" and stay like 20 minutes on me just being still inside me till he gets up put his plug in me keeping his sperms in me and says "your leaked drops and my sperm are going to be your breakfast tomorrow , good night sweetie" and we both have our best kinkiest sleep of our life i guess , and i have the question in my mind , what is he preparing for me tomorrow ?

So about a year ago , i was in my penultimate year of college ,trying to cover my living expenses , room expenses which I became alone in after my roommate went back to his home country as a gap year , as you know he was my very close friend we were in this friends with benefits win win relation , no strings just all friendly and warm , he was the only one knew my sissy side and he paid most of room expenses so i didn't care about work hours that much , but fast forward when he left me i missed him as a friend, and also i had to work more hours just to get basic expenses , and of course i kept in touch with him online I did enough money , but almost studied nothing in that first semester on my own , just did classwork assignments to get any grades , but the main projects was much difficult to do on my own , I started searching for some teams cause i know i can't do it on my own in small time and with such small studying knowledge , i got into some teams for all courses except for two courses. I tried looking for any friend i know but no one enrolled in neither.

I did not know what to do at such point and decided i start studying until i figure it out , through money i made in first month vanished part by part , i had two options back then to quit both courses and make some money on studying time or quit college and be a sissy sex worker "kidding" or ask some strangers i don't know well in both courses for this projects as a favor , so while chatting with my roommate , he suggested i check with some nerdy close friend of him he said he may agree for such thing ,and he'd give him a call but i shall offer him some of my cake cause he's a bit kinky, and we both had a laugh about what i thought was a joke and i decided i'd give it a try maybe the nerd would agree just from knowing his friend referred him to me , so maybe who knows?

I knocked on his room door ,wearing normal some what tight jeans but nothing erotic, he let me in , and we had a talk about semester , our friends and he seemed a bit introvert , somewhat handsome , normal body which i prefer and his room was clean and tidy, and i felt cool around him, he told me he had a gf but they broke up and his now also alone in his room and offered a cup of tea , i said water is fine ,he came to me walking while sitting and having my glass of water and gently moves my head up with his hand on my chin to be in eye to eye contact, saying "i know your financial and courses situation and your problem in projects but if i let you with me as a team member what would you give in return if the project is already finished? , I know you're bisexual ,correct? ", I said yes I didn't even have another response in my head but began to form a thought on what some weird hole i'm falling into, he says "i'm also bisexual and i'll be real honest with you I kinda want a sexual favor from you that's it , and then both of us will never get in contact together even projects are to be submitted without any revision you'll get the grade you want" , I was left speechless starring at him , don't know what to say , he says "i don't want your response now just think of it" and here's the kind of favor i want specifically and he hands me a pink neat paper , says "i want you to read it carefully tonight and decide whether you're into it or not then get back to me and whatever you good or not it was nice knowing you, sweetie;)" i was a bit stunned but decided to get out of his room and see wtf is going to happen then ,tbh i did not feel scared at all he speaked direct and without any lying he stated his purpose so something for something but of course i want to see what's he into

Something that motivated me even more was my sexual frustration , I told you no roommate to pleasure me , no "back then" current boyfriend , closeted sissy in rural area in belgium , so getting into a good warm relation was difficult , additionally i don't have time for such thing , so all i had was my pink diamond plug , pink cute cage and my pink dildo i mount everday during shower or ride while studying , and the schedule i was on to lock myself all week except for thursday to get to relief myself whether from mounting the dildo or with two-finger playing so maybe being horny affected my decision later ,I decided any bdsm stuff would get me to decline his offer no thinking cause that's not my cup of tea ,anyway i get to read the paper and I get a bit stunned but also hard in my cage , you know that kind of excitement where you feel like you small hard clitty would get broken from the cage any sissy tried chastity would get it ;) , the pink paper is divided as 3 parts : program synopsis , which states that i have to spend one day with him and to obey the rules in second part and any breaking of rules leads to repeat the day ,the program targets enslaving me to be as obedient pet whose goal is satisfying and obeying rules and orders i take without refusing and after the end of the day the program is finished and i get what i desire .

coming to the second part which is the rules i got more interested : spend all day on fours , spend all day caged , fully naked , whatever ordered should be done , you can use your hand normally , but only if it's for sissifying tasks or accepted deal from your owner ,like using a fuck machine or turning on some hypno while room-alone, no single word , your orders would be to give a blowjob or moan if ordered to and some other similar orders , anything leaks from you or your owner is to be licked all from the floor , you'll also act as a maid , so some kitchen parts would be in your level in case you're ordered to make some tea or food , but all while on fours , no taking off your collar ,and sleeping on floor, and you're expected to come fully clean , will sleep on floor beside your master and start your day normally according to rules, side note there would be a camera on 1.5 m level viewing all room just in case you break the rules and stand third part included a small message saying : "all done in friendly and kinky play nothing violent , just all role play and we can even decide a safe word if wanted nothing serious we just having fun" , I finished the paper at midnight and i found my self humping my bed with my caged clitty and there's a huge cummies leak circle around my clitty , at this point i knew i liked it , but i decided to give my roommate a late "pretending to be upset" call to be sure he's safe for being around , and my roommate tells me "i told you i knew he's a bit kinky and also he's into sissies but i can ensure he's really not a serial killer he just wants to have some fun". and by that call i decided to go for it , cause i don't wanna to drop the courses and tbh that's not the only reason;).

I get myself ready with my cage with me , and butt plug and dildo ,cause i don't know what he has , and i get my pink bag on with normal clothes and go on about 7 pm knocking on his door he opens and let me in , before he starts talking , i interrupt and say ,ok i agree but after this we don't know each other and i pass both projects , he smiles and says ok we good , he takes the paper and tells me can you sign it with name kelly , i said ok whatever , and tells me gimmie one second and he gives me a blue diamond plug and a pink dildo and fuck machine saying he borrowed the fuck machine and he's gonna return it but i can keep the dildo and plug as a gift he bought for me after the end of the day ,tbh i really got more excited because i never got to try a fuck machine before, then he gives me a pink collar with a rope attached to it written kelly on it , and says "i assume you read the rules you can go to the bathroom and get yourself ready and we'll start at 9 pm " and he gets off all of his clothes saying "see no problem no need to be shy" , I say ok and get a glance on his dick it's good size and the size that's going to pleasure you normally so neither huge which is sth i don't like nor small which is comparable to my dildo which i use daily , so perfect fit. i get undressed in bathroom had a shower ,get the collar around my neck and my own cage on my clit then trained on the mounted on wall dildo of mine and kept it in case get bored then play on my phone while thinking how would this day be , what can happen and then my timer rings and it's 8:55 i get on fours like a good sissy as he wanted , and practice walking on fours while plugged and caged, then at 9 :00 he opens the door found me and says "good girl , see it's gonna be very normal don't worry you might even get bored" i shake my head , cause remember the only sound i can do is moaning , so he grabbed the rope of my collar and walks a bit with me walking around the room then stopped at his desk where he had mounted to its side his blue dildo he says take it in your mouth while i finish some assignment , i start licking it infront of him then he ignores me at all while i keep sucking it for almost half an hour while keeping this doggy posture position of a good girl sucking , then he gets up and looks at my tiny clit leaking a bit on floor and some of my saliva getting on floor from sucking , he says "lick all you leaks till i take a shower and get ready for you", i looked on the floor and saw my leaks and instantly starts licking it all with my stupid clit not even stopping , and get back to sucking the blue dildo , and after 10 minutes ,i hear shower stops and he gets out all naked and he gets the blue dildo and mount it to the fuck machine ,removes my plug, and gets me from my collar in such a position he's sitting on his bed and i'm facing his dick , and the tip of dildo is almost in me waiting to be fully inserted , he says "come on taste it " , and while on my fours i only moved my mouth up and down on his dick and even he tries to hold my head to position it correctly , not deep throating he was super gentle but just position it correctly then starts the fuck machine on low speed , i start feeling it in me while sucking , so the start of my spit roasting , some inner sissy urges starts in me you know that feeling when you're on your way to sissygasm , my moans get's a bit hearable then he gets the machine on higher speed while fixing my head and basically fucking my mouth , my moans and gagging on his dick gets louder with higher urges and feeling , i'm gonna explode from my tiny clitty with a lot of cummies then on highest speed , i can't control myself , full ecstasy and horniness , i can't feel but the cummies on the door of my clitt while he speeds his own fucking speed then while all that happens , i explode first while all on my fours , of course i can't see it because i still blowing him but i can describe it as intense stream of what i saw later to be semi white cummies , and i call it cummies cause even if quantity is big , this is still sissy juice that comes from sissy pleasure while caged and limp and getting penetrated not in a man position but i dropped for like half a minute non stop , and about the feeling , you're basically in heaven , anyone tried sissygasm would agree , anyway i was not in a position to update with my sissygasm and see my cummies on floor until five minutes later when he takes his dick away from my mouth and gets his cum on floor , then he lays on bed and says "you know your duty ,cutie" and then i instantly get to lick all his cum and my cummies not wasting any part of it even the machine was working on medium speed then he says "you get to sleep under me when the machine timer stops" and spanks me a slightly loud spank with his hand that i even leaked more and he turns off the lights , 10 minutes later , the machine stopped , i found a pillow and slept on my belly , my tiny cute clit was even horny i checked it before sleeping but tbh i was low key frustrated that he didn't fuck me himself , then i get to sleep , 2 hours later maybe on 2 am , while i'm fully naked while on my belly , feel his hands on my ass grabbing it , and his mouth kissing my neck and cheeks saying "i told you'd sleep under me " his dick was hard and its length was along all my ass crack plus my tiny clitty which was pointing backwards while my all body was touching the ground , he starts fingering me and telling me no moaning , cute slut , and since it's an order i bite my pillow instead to avoid any repeating , tbh i lowkey during the whole experience wanted a repeat , but he updates the fingering first one finger and revolving around my hole , then in and out then two fingers and all i can do is humping the floor and biting my pillow , then he says "now you're ready" and firstly he adjusts my position instead of my belly is the part touching floor he put my clit under my belly and the remaining area of body still touches the floor , so my clitty is between my belly and floor and most of our weights is on the poor caged clitty movements would break it more (i already had reached the point where i cum limp while 2 finger playing since 2 months from this night so no problem from further breaking) ,then he starts adjusting his dick with his left hand while spanking me and kissing me , and bit by bit he's in me while i'm fixed and just biting my pillow , then he rests for 5 minutes and starting the rough fucking , now my points of pleasure now isn't only my hole but my neck his kissing , my poor clitty which is moving with our weights on it , but luckily the floor was a bit soft not rough to hurt my skin , then he goes faster and faster and i again feel my clitty leaking alot , that's the first time i sissygasm twice a day , and he goes more fast and rough at 2 am while no sound is coming up from me , so the only sound you can hear in the whole dorm his body hitting my red slapped cheeks or his spanks , at this part i'm being used and that's the goal of his program which popped to my mind until 10 minutes later i feel his dick pulsating in me and he kisses my neck says "thanks sweetie" and stay like 20 minutes on me just being still inside me till he gets up put his plug in me keeping his sperms in me and says "your leaked drops and my sperm are going to be your breakfast tomorrow , good night sweetie" and we both have our best kinkiest sleep of our life i guess , and i have the question in my mind , what is he preparing for me tomorrow ?

Ok so 3 years later I moved to belgium for university scholarship , the monthly allowance was not high , so i had to share dorm with some one , he was a guy , older than me by one year , normal body but seems a bit shy , later on we got close as friends i was closeted sissy back then, but told him i'm bisexual out of fear maybe , donno ,he was cute but he was hesitant about dating girls fearing he would mess it up , at such point he still didn't know much about how slutty i am , nothing about my dildos and cages & plugs

Till one day came , it was weekend and i was alone in room , totally smooth , riding my dildo with headphones on hypno, and caged as cherry on top and I thought he'd be out for some long that was his habit in weekend hanging , but he came and suddenly door opens he looks other way apologizing and i tried to take some clothes on quickly , this was the first person to see my sissy side , i was embaressed a bit but fuck it thats me , we sat later and he said it's cool no problem , and i can be as i want in room when he's around and act however i want , that triggered some horniness in me being little girly , like i didn't go for lingerie or sth but boy shorts , panties under flared pants & leggings some small makeup and one by one he started getting me presents , body lotion & splash , and gradually i started taking more of room work for both of us , i was more comfortable cooking for him & doing laundry but all casual and friendly

Things got spiced up ever since that one time i was cooking and couldn't reach the salt container in the upper side of the shelf in kitchen , then i felt his dick literally pushing me up as he was trying to help , i leaked at this moment a lot and remember getting off like 3-4 times that night on such fantasy , ever since then this moment repeated a lot , and similar stuff i started getting from shower with towel almost covering half of my ass , if he passes by , he would gently spank it ,and we both would have a laugh , touchy stuff happened more and more , cage and plug got normalized for him to see me even fully naked if by mistake or me even started leaving door un closed while naked lingerie got out sometimes and he was fine flirting with me , still at this point he'd say he's straight , we both know he's lying

Then he comes up to me at night while we talking before sleep that he'd start a casual dating but he's hesitant about the sex , so i who was single for 5 months came out with idea , do you want a training buddy ? , and it's not gay at all if you're with the hot chick you're calling me every time you see me correct? , and then out of no where i saw him get up pull his bed which was on the other side of room to be beside my bed like it's a big bed , I in my thong covering nothing had my cover on to cover my body normally and I got shy and gave him my back he kissed my neck from behind and i gave no response , not out of shyness but i just didn't want to appear slutty , then he kisses my ears and get his chin on my upper side of back gently asking "you good"? , a very femme , and high pitched voice came out of me saying 'yes , i'm fine' then i feel his hand taking my hand putting it on his hard dick , he get his two hands one under my body to lower tit and one on the other tit , i started moaning hard and tweaking and leaking and also i started feeling his precum on my hand , so extra lubricant yay , so while kissing my cheek and neck he got his hand on my caged cliity and other on my pink diamond butt plug removing it , and he tells me , cutie insert it slowly yourself and i start putting his dick in me bit by bit till fully in , he got the keys of my cage from the necklace on my neck and said , i'll give you one release as a good girl so he removes cage , asks me to spit on his two fingers and just take those two fingers to relief me while fasting up his fucking process , i bite on my pillow , not from pain but pleasure and he goes non stop on like 5 minutes till we both get very intense , and i cum almost at same time i feel his dick pulsating and breeding me he even from the tense of climax pressed a bit more on my clity , but i don't mind , after that he got on his back exhausted , same for me , and he speaks while looking on roof "i might be bisexual" ,we shared a laugh and slept as we are

ever since we only have sex to satisfy and relief each other it's all friendly not like it's free use or sth but out of love , he got better in his casual dating , and whenever he & I become single or available we go for like a casual sex period , till something new pops up , we went through this stage 6 times in 2 years , unluckily he finished his degree and went back to his country but we still in contact , i really consider him one of my loving friends i'd trust fully , what i really miss was his rough & gentle spanks he'd give me while passing by or even during/after sex no one i dated did it the same way ,i hope all of you get to experience such journey

1-Wasting cum that comes from partner whether he's breeding me or it's on floor or face , I swallow and lick it all what so ever , and after any breeding session I use my pink diamond plug instantly to avoid any leakage or dripping

2-treating my clit as a dick , Always I sit to pee , never hold it with more than 2 fingers when allowed to relief myself which is scheduled of course , we'll get to it

3-getting off my chastity during locktober , even when cleaning I just point the shower to my lower part while having it on normally so the soap soaked my belly gets down on it and clean it normally so even cleaning is not difficult with chastity on , I on 3 months for this rule and I gotta tell you this is the peak of controlling yourself

4-wearing male clothes when alone , always lingerie or femme causy clothes or fully naked , if I'm playing with myself

5-pass a weekend without getting myself spitroasted , so I don't go hooking that much , but after having my 2 lovely all time favourite dildos and getting myself spit roasted every weekend while listening to hypno , one mounted on my facing wall in my mouth and other on the wall behind me if it's a doggy position, I always try to make the margin narrow to get the dynamic of synchronising the dildos coming in and out just from going back and forth

6- breaking the one time relief per week rule, if I lose to my urges while not locked I lock myself for a complete month as a punishment, so simply treating it like a new locktober

7-wasting my own commies, if I not training for sissygasm and just touching my clit with two fingers , I usually do it as if if I'm milking myself in doggy style with my left hand two fingers , and having an ice cube tray under me ,and use it for later in a soup , coffee , or even as ranch sauce it's almost very similar trust me , sometimes I'd take it fresh from my clitty to the food I'd be eating

So those are my sins , I try to prevent myself from in order to feel better about myself ,I hope you try them on yourself and tell me how much it changed you

what are yours!!

1-Wasting cum that comes from partner whether he's breeding me or it's on floor or face , I swallow and lick it all what so ever , and after any breeding session I use my pink diamond plug instantly to avoid any leakage or dripping

2-treating my clit as a dick , Always I sit to pee , never hold it with more than 2 fingers when allowed to relief myself which is scheduled of course , we'll get to it

3-getting off my chastity during locktober , even when cleaning I just point the shower to my lower part while having it on normally so the soap soaked my belly gets down on it and clean it normally so even cleaning is not difficult with chastity on , I on 3 months for this rule and I gotta tell you this is the peak of controlling yourself

4-wearing male clothes when alone , always lingerie or femme causy clothes or fully naked , if I'm playing with myself

5-pass a weekend without getting myself spitroasted , so I don't go hooking that much , but after having my 2 lovely all time favourite dildos and getting myself spit roasted every weekend while listening to hypno , one mounted on my facing wall in my mouth and other on the wall behind me if it's a doggy position, I always try to make the margin narrow to get the dynamic of synchronising the dildos coming in and out just from going back and forth

6- breaking the one time relief per week rule, if I lose to my urges while not locked I lock myself for a complete month as a punishment, so simply treating it like a new locktober

7-wasting my own commies, if I not training for sissygasm and just touching my clit with two fingers , I usually do it as if if I'm milking myself in doggy style with my left hand two fingers , and having an ice cube tray under me ,and use it for later in a soup , coffee , or even as ranch sauce it's almost very similar trust me , sometimes I'd take it fresh from my clitty to the food I'd be eating

So those are my sins , I try to prevent myself from in order to feel better about myself ,I hope you try them on yourself and tell me how much it changed you

what's yours!!

There are some vintage relatively old videos that have this lady or group of ladies totally feminizing a boy to be Totally cute princess , then the sissy get introduced to her man or even pegged by this lady , I found myself adoring this type of videos/ captioned pictures or magazines , do you have any suggestions you'd give me in that?

So , the trivial thing for clothes , that both genders learn about dressing and clothes at young age and get a lot of info about any type of clothes they could use , but when a sissy wants to learn , all I see is about panties or lingerie, Is there like a full femenization /dressing and general behaviors course or video our there , I don't care if it's a program or part of a video for a domme & sissy on a porn website , but at least it conducts the feminization scope like a lady group handling a sissy in those vintage videos ,any recommendations?

like i see some veds the clit of a sissy is self pushed by finger , not talking tucking and i don't even know its name but i can't do it i find some resistance what direction to i push the tip of my clit deep into up or down?