sissy experiment @myfirstsissy - Tumblr Blog

kingjaffejoffer

myfirstsissy

dumbasses i'm still waiting for them to see the light.

i wonder...

are there any apps oit there like tumblr that do still allow nsfw content?

any reason why i can't see nsfw content anymore on tumblr???

diary part 5 "the restaurant"

so after having our little fun in the club and having some fun back home i waited a week.

after one week, on a friday night i shot my sissy a message telling him to put on girly clothes, high heels, a wig and no underwear. offcourse he/she thought we where going to have some fun at his place.

i can't help but think how silly he looked realising we where actually going out again 😂😂😂 only this time he was in full ensemble. he was verry reluctant and did not want to at first. i said nothing to the backtalk and started opening his pants, his caged clit exposed, frontdoor wide open.

"needed to see if you're still wearing it" i said. i could tell he did not know how to react, and i loved that. at this point i knew that me touching him down there had him weak on his knees and i could pretty much do anything with her.

he agreed after i told him i had a place in mind well out of town, he knew nobody would recognize him and he felt more at ease that way. i didn't really care i just wanted to fuck him in public again.

i parked my car in a underground parkinglot and we whent up to the main street where there was this fun little restaurant. i knew he didn't have much money for the rest of this month a'd wanted to give him something nice while i was getting something nice aswell.

i orderd us a three course meal with appetisers and some champagne. during the course of our meal he told me he never ate at a fancy place like this, i told him that a fancy girl like him should take care off herself and always has a mean of good income with an ass like his/hers. offcourse he is still way to nervous and reluctant to sell himself off to strangers. wich i get and i wouldnt press him on it aswell, in the end it is still his bodie.

anyway we enjoyed our meal and had a little chat about the whole project. i could tell he felt at ease and was happy i can only think it was because nobody there knew him or couldnt tell that he was actually a guy wearing sissy clothes, as a matter of fact. he got some looks when we walked in and not at all because he looked manly if you know what i am saying ;-)

during the main course i felt his foot tap my shin, yet this didn't feel like the high heel shoes he was wearing, this felt...softer. at first i thought it was by accident but soon i realised that it was anything but an accident, she placed his/her foot against the shin of my right leg, i looked up at him, one eyebrow raised, he looked at his plate and contineud eating. i remember smiling a little and enjoying the fact that he was this sneaky about it.

i felt his foot verry slowly....no...extremely slowly crawl upwards so that after a while i felt his foot slide along the inside of my thigh eventually reaching my half hard bulge. i have to admit this was the first time anyone ever did this to me, i mean you read about it on ocasion or see it in porn or whatever but to have this actually happen to me was odly exciting. my half hard dick soon started to swell up in my pants wich since i was wearing a three piece suit was verry thin fabric so i could feel every twitch or turn of his foot against my crotch.

somehow while i was growing in my pants he found a way to lay my cock in such a way so it was growing along side my leg. my cock twitched and pulsed in my pants as he was using his foot to run along side my shaft stroking it up and down. i got so hard i'm shure that if i stould up at this point everyone would clearly see my huge bulge in my suit pants. i enjoyed the feeling of his foot rubbing up against my cock, all of the sudden our waiter was standing next to us and said "did you enjoy it?" halfway shocked and confused i looked up at him and suddenly realised he was talking about the food and not the foot that was STILL rubbing my cock through my pants. i closed my legs as to give the sign to stop, he/she did.

"how's the caged clitty doing" i asked him after the waiter left. he told me it wanted to be released and i replied with "one more week until no fap november ends, we're going to do something special for you then." he looked really excited about it and had a big ol smile on his face.

he asked me if i liked what he was doing and if i wanted him to do it some more. i told him that i liked it but i didnt want to do it for now but that this did pent me up quit a bit.

at any rate, i let it go and enjoyed my desert. after we where finnished with dinner i paid and we got out of there to the underground parkinglot. ariving at my car he was gonna walk around the car and get in the passenger seat. before he could step one foot further away from me i grabbed him by the wrist and pulled him close to me holding him by the waist. "you didn't think you'd come of that easy did you?" he swallowed and looked with a weird smile at me "i was hoping not." he replied.

i kissed him firmly on the lips and our tongues intertwined with each other, i think at this point we where both verry turned on and needed to play. i have one of those high end bmw's so the hood was verry high up. i picked him up and sat him down on the hood of my car, totally forgat the fact that i told him not to wear any panties. his skirt crawled up and i could see his bare ass and caged clitty lying there limp resting on his balls. the fact that i forgat and this came somewhat as a surprise got me even more excited and i got hard as a rock. i was going to open my pants but he leaned forward and grabbed hold of my hands and pushed them away from my belt and zipper, his hands took over as he opend up my pants, slid his hand into my suit pants and grabbed hold of my warm rockhard cock. he slowly jacked me off in my pants for a bit and then lowerd my boxer and pants so my balls and cock where hanging out of my pants. he looked at me, spit in his hands and proceeded to lube my cock up with his spit, when it was all wet and slippery he guided my member towards his tight little hole and let the tip of my cock rest against it. he then laid himself back on the hood of my car hands next to his head, skirt all the way pulled up. i liked the initiative this time and slowly pushed my hips forward and entered his ass, at first i whent slowly in and out to go deeper, by the end i was thrusting in and out of him so fast that you could hear my balls slap against his ass. he enjoyed it so much he started moaning loudly and the echoe of his moaning reverberated throughout the parkinglot. i would ocasionally lean forward to kiss him bit mostly didn't because i enjoyed the vieuw of my fat cock penetrating his ass. when i felt myself get more swollen down there and got closer to filling him up with a huge load, i reached my hands under his legs and grabbed him by his thighs. pulling him into my cock i felt myself getting so close to orgasm because i was so deep inside him and felt his hole tighten around the thickness of my meaty shaft. with huge spurts of cum i came deep inside him. keeping my cock inside as it twitched and spurt stream of cum after stream of cum filling him to the brim. as i pulled out a big wad of cum followed dripping out of his hole. we panted and moaned at the last bit of extacy we felt. after that we both happily got in the car, not much was said during the car ride home just a few smiles and giggles on his part. i dropped him of at his place and with a final "thank you sir." he got out and left, me watching his ass sway from side to side while he was walking towards his house, i grinned, turned on the engine and drove off.

i hope you guys enjoyed our latest little escapede :-) if you did and you're reading this please be so kind as to like and reblog, it would help allot 😘 thank you.

thinking...

i'm thinking about giving personalised sissy assignments but don't know how i could make that work for everyone. at this point there's quit a few people reaching out asking me to be theyre dom and such, and i want to have fun with you all but might have to concider starting a peronalised sissy task thing. any idea's guys?

diary part 4

allright sissy's and dom's, here's what happend saturday night.

so as you all know my sissy didn't have money but wanted to go out. me, not lacking any money any time soon decided to have a sort of exchange of services with him/her. i pay for what ever he wants, he does whatever i want 😈😈

as far as deals go, not a bad one at all.

first we had to decide what he wanted to do and how far he wanted to go because me sissy is still not out of the closet and is not embracing the sissy life out in public...yet.

i decided on having him wearing one of those penis cages and some female panties would be satisfying enough for me to torment him a bit.

we decided on a club outside of town so noone would know us, there wouldnt be much light, the place would be packed and booze would be plenty...in other words, the perfect place for me to have some fun with this cute sissy 😁😁

when we arived i shut down my engine and asked him if he was wearing what we agreed upon, he answerd with a shy yes. offcourse that wasn't good enough for me so i decided to tell him to show me, and so he did. he looked around to see if noone was around the car and give me a sort of nervous half smile, opend his pants and showed me his satin pink striped panties and after i pulled those down, his cage where his clitty was hanging in.

"good" i said. and proceeded to kiss him on his lips verry soft and slow for a second or 2.

he grinned a little bit and we both got out of the car after closing his pants up again. we whent inside and i could clearly tell he was feeling verry nervous about all of this he was almost looking like he didnt have any pants on and was walking around in those cute little panties for everyone to see.

we whent to the bar and sat there for a bit having small talk and just genuinly have a good time. the more he drank the loser he got in the things he was saying and i have to say i don't know if i liked the teasing from his side, it felt foreign to me, but since this was his night and he got to go out n have fun i decided to let it go.

after a while he got up and whent dancing, me not really big on dancing stayed at the bar looking into the crowd for a little bit. after a good 15 - 20 minutes all the sudden a cute little ass was in view right in front of me. it was swaying from side to side and was moving somewhat sensually to the beat of the music, i would recognize that ass anywhere....it was my sissy's ass.

i can't really explain what came over me but got up and left my seat, stood right behind him and grab hold of his hips. i don't know if it was the booze, the music or just the fact that his cute lil ass swaying in front of me. but i needed him to know what i was feeling and what i was feeling was turned on, horney and goddamn hard as a rock.

he immediatly knew it was me standing behind him and he sort of leaned back against me chest. i didn't mind and we kept swaying to the music, with every beat our bodies pressed closer togheter until at long last his butt was pressing deeply against my rock hard cock.

at that moment i was shure of only one thing, i wanted his ass and i wanted it right now.

i remember breathing heavily in his neck, grabbing hold of his wrist and just started walking outside without saying anything. i really didnt look or mind how he reacted to me walking that fast towards the exit but at this point my mind was set, i wanted his ass, he was my fucktoy and i would fuck him nomather what.

once outside i walked him (still holding his wrist) in an alley not far from the club. once halfway through the alley i stopped and turned around, now i could see what he was reacting like, the little fucker was grinning...he was just fucking grinning... he probably felt my urge yo fuck him and it gave him a sence of power i presume...a false sence of power, the only thing i could think was "this little sissy is gonna suffer" i grabbed him by the hair, pulled his head back and said "you are my fucktoy, right?" he swallowed audibly and his sence of power was swindeling. he knew i was in control here. he said "yes." "then act like it!" i said as i turned him around putting both his hand up against the wall and pulling his pants down, his bare ass out in the open and bare for all to see. his little clitty dangeling in between his legs, useless and limp. i opend up my pants and whipped out my throbbing cock and let it rest on his back pushing my balls into his buttcrack.

i felt him pressing back wich made me even harder, not only did he not mind me beeing this rough with him, he even liked it to.

since i had no lube on me...(jeesh i wonder how i could forget😈) i spat on my own dick and rubbed it open over my shaft i psuhed the head of my cock against his tight little hole and started pushing inside slowly as i entered i could hear him moan and gasp, it didnt take me long to start going in and out of his asshole faster and faster, i could feel my own dick getting harder and thicker as i thrusted deeper inside his hole probably hitting places he didnt even know he had.

the urge to cum fell over me like a summer storm, i was gonna fill his hole to the brim and i was gonna do it now. with one last thrust i ejaculated so deep in him i swear my balls where against his ass. i moaned and breathed heavely down his back as i enjoyed the last twitches my dick gave inside of him releasing the last spurts of cum deep inside.

as pulled my dick out i looked to the right i saw a guy, fairly young standing at the end of the alley just staring at me. he said loud enough for me to hear "you guys had fun?" i threw up the good ol rock n roll handsign and exhaled deeply. the guy whent on his way that, he probably just stood around to enjoy the show.

my sissy was still panting up against the wall and a i pulled up my oants and boxers i could see that his little cage was still oozing...i kneeled down to where his caged dick was right infront of my face, lifted up his caged clitty with one finger and said "it's a shame you can't cum during november, beeing like this must be hard for you" i looked up at him and he looked down at me. i could see in his eyes he wanted release so bad and probably wanted me to suck him bone dry. "i started pulling up his pants and cute sissy panties and just said "ah well,... two more weeks" and with that we whent back inside and enjoyed the rest of our evening drinking and having fun.

so there ya go peepsies, i hope you guys liked it. btw if youve gotn this far would you be so kind as to reblog this diary to help me grow on tumblr and find other sissy and like minded people, i'm really having a blast witht this and honestly, don't want it to stop ;-) thanks. 😘

sorry for no post about what happend but we did go out togheter!!!

story will follow tomorow ;-)

thanks lil sissys 😉

to all the sissys that allready sent in theyre cute lil sissy pics. thanks :-D you're all so cute.

hehehe ill get em there i'm shure 😈😈

sissy's should read this...

if you are a sissy and you want some excitment in your life and since i can't meet up with my own sissy for the moment beeing, here's a little assignment any good sissy would do like the little cocksluts they are. i want you to put on your sexiest sissy clothes, take a sexy pose and take a pics of yourself, send it to me in my dm's and i will rate your sissy ass. you can blur out your face or whatever you need to do to be oke with sending me a pic but just get it done. i might end up sending you a little something something in return ;-).

300

not the movie but what this blog helped me reach in a good 4 weeks :-) thanks guys 😍🤩 and keep it up!!! let's get some reblogs up in this biatch!!! xx

diary part 3

i pulled up at his house around 22:00 and walked up to his house. this really wadn't like other times because when he opend his door i walked inside and i decided to have a little chat with him. i knew he was expecting me to do something and if there is one thing ive learned in this experiment it is that i should on ocasions not give in to his/her desires.

she is still my plaything and i want her to know that this is about my enjoyment with him. his enjoyment should come from serving me as that is a sissyd rightfull place.

the conversation moved us to the no fap november that we've talked about in our messages. he told me he was having a hard time and that it was difficult not to touch himself especially when he thought back to our incounters, wich according to him happend regularly.

i said nothing about it in the end, stood up and grabbed his hand and pulled him of the couch. he visibly swallowed and i wonderd how harf his clitty allready gotn thinking about what was gonna happen.

i sat down where he sat on the couch and spread my legs while i pulled him by his hand down on his knees. at this point i could clearly tell that he was allready having a hard time because he wasn't looking in my eyes anymore but straight at my bulge. i closed my eyes and laid my head back on the backsupport of the couch and said "remember....you don't get to cum..." all he said was "oke" but i could hear by the sound of his voice that he wanted to so bad and this moment was only going to make it worse for him.

i felt his hands slowly open up my zipper and unbutton my pants. after that i felt my hard cock freed from my boxers and a hand softly grab my shaft to lift my dick from my belly on wich it rested. a wet sloppery tongue continued to runs along my shaft from the balls all the way up to the tip of my cock.

i have to say, that warm, wet slippery feeling made my dick instantly allot harder and made it grow in girth a little aswell. he proceeded with putting his wettend lips around the head of my cock and started to go down slowly. there is no other feeling in the world as to feel a warm slippery mouth slide down your shaft. he kept going at it end move his head faster up and down, he was really getting in to it aswell as i felt him put so much passion in his movements. must have been his own pent up sexual desires without release that eventually pushed him to sucking, licking and slobbering over my cock like a madman. after a few minutes andending up with a verry slobbery cock i stopped him and pulled my boxers back up.

"take off all your clothes and go get the lube" i said.

he did so and after comming back with the lube he took off all his clothes. i told him to sit on my cock that was still hard and now back in my boxers and told him to lean forward. he arched his back,bringing his ass up a little bit and rested his head on my shoulder.

i then drizzeld the lube over his ass and told him to grind me in my boxers as to make me cum because as you all know someone wanted to buy my cumstained boxers...wich btw...still weird 😂😂. but whatever.

he plopped his lubed up butt right on my cock so my shaft was lying down on my belly and rested in between his asscheeks.

there was enough lube covering his asscrack that i was starting to seep through my boxers and i felt him start to move his hips forwards and backwards. the lube that seeped through my boxers felt so great and it was undoubtably a weird sensation but still a good one. as he started to go faster in his movement i saw his little clitty get so hard and was twitching and moving and jumping with enjoyment i swear this must have felt like torture for the poor boy. but it didnt stop me from grabbing hold of his sissy clitty. as i did that i heard him gasp audibly and told him once again in a firm voice "you will not cum".

between a gasp and a moan i heard him whisper "yes, mister" knowing he had such a hard time made the intire thing so much more exciting. after a short while of feeling my dick slide in between his soft asscheeks i came and filled up my boxers so much.. my cock twitched and throbbed as i grabbed my sissu by the waist and held him from moving around on my dick longer. i rested up a little while as he sat next to me on the couch saying nothing and still hard as a rock.

i took of the boxers and took a picture of it to send to the tumblr follower to let him know that he was gonna get his "present" soon.

my sissy had put on a robe and walked me to the front door, before i opend the door i turned around let my hand slip in his robe to grab his clitty, looked at him and said "you're halfway there you're doing good" i kissed him on the lips, not to soft not to hard and played with his dick a little bit and made it hard again. i let go of his lips and he sighed deeply. i gave him a cheeky wink, opend the door and whent back home.

tho i have to say it was a weird question to ask, i would do it again just for the experiense of that feeling 😂😂😂 it was, in one word...fun.

the buisness meeting.

i'm sitting in a business meeting at the moment, hard as a goddamn rock and i'm pretty shure if i stood up, everyone would see my rock hard cock through my business suits pants :-s something sort of weirdly kinky about this tho

got a question.

just got asked by someone in my dm's what i am. not a bad thing to clear that up for a sec.

i'm a bisexual guy, i just love sex. hard, soft, male, female it doesn't matter to me, but goth girls will always have a special place in my heart and hopefully my dick will always have a place in them 😂😂🍆🍆😈😈

#goth #gothgirl #gothgoth #goth chick #goth girl #sex #gothic #goth makes girls go bad #sexy #sensual #choker #choke play #choke me daddy #chocke me #goth porn #goth nsfw #goth sex #goth 18+#goth choker

so i made a decision with that boxers request ;-) hope youlle like it you weird fuck. (you know who you are) 😂😂😂

the...offer?

someone just asked me if my sissy could make me cum in my boxers and then send the jizz stained boxers to him for money.... should i do this? i mean i don't mind and 20 bucks is 20 bucks but thahaha lol you guys can be so weird. i like it! anyway, should i?

i don't think my sissy knows what she signed up for....

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