https://pornmeka.com/tags/babysitter-diapering/ Wed 15 Apr 2026 02:11:35 +0200 https://pornmeka.com/videos/1540896/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-mp42/
 **top #34 c4s video- #1 in diaper discipline** your stepmommie katherine adores looking after you, but as she’s done in the past, when she has things to do, she surprises you with a special treat by periodically bringing in a new babysitter.   this time, it’s shy and pretty college girl, claire.   you’re a little extra nervous because even though you’ve had a crush on her forever, you have heard rumors she has very creative ways to deal with dorky, pathetic, diaper wearing wusses like yourself.   you are really nervous as you suspect claire will quietly tell all the neighbors if you don’t do exactly as she says, so you try to be really good.  claire brings you to the pool and attempts to take you to swim.  you get embarrassed as you’ve always been shy about getting into the pool since you are diapered- especially with a pretty girl like her.   claire sweetly teases you about your shyness, tells you to stop being a big baby and tries to coax you to get into the pool.   you still hesitate, so in playful frustration claire makes you a deal:  "since you're double diapered, she'll double diaper herself to show you if she can get in the pool with diapers on, you can do it too”.  she proceeds to slide off her bikini bottom, doing a mini striptease, then grabs two of the diapers out of the diaper bag and seductively puts them on herself to demonstrate.  you stand there watching her, stunned with a stiffie.clearly if you want your swim trunks back, you'll have no choice but to join her in the water!  tsk.. tsk.. tsk.. what a "dilemma"... poor widdle diaper boy!  will you be able to resist making creamie diapers as she sweetly teases and humiliates you ? only one way to find out!enjoy! xo includes:  diaper lover, age regression, adult diaperwith:  clairemore from domination for your own good: ab step-mommie and eden diaper and encourage you to mess your diaper at portrait studio tailgate party diapering! diapered on game day by stepmommy katherine as stepsister shelley & her friend claire watches on and helps! naughty nite nite with step-mommy ]]> Fri 23 Jan 2026 16:07:48 +0200 https://pornmeka.com/videos/1540896/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-mp42/ https://pornmeka.com/videos/1501044/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-wmv/
Click for mp4 version **top #34 c4s video- #1 in diaper discipline** your stepmommie katherine adores looking after you, but as she’s done in the past, when she has things to do, she surprises you with a special treat by periodically bringing in a new babysitter.   this time, it’s shy and pretty college girl, claire.   you’re a little extra nervous because even though you’ve had a crush on her forever, you have heard rumors she has very creative ways to deal with dorky, pathetic, diaper wearing wusses like yourself.   you are really nervous as you suspect claire will quietly tell all the neighbors if you don’t do exactly as she says, so you try to be really good.  claire brings you to the pool and attempts to take you to swim.  you get embarrassed as you’ve always been shy about getting into the pool since you are diapered- especially with a pretty girl like her.   claire sweetly teases you about your shyness, tells you to stop being a big baby and tries to coax you to get into the pool.   you still hesitate, so in playful frustration claire makes you a deal:  "since you're double diapered, she'll double diaper herself to show you if she can get in the pool with diapers on, you can do it too”.  she proceeds to slide off her bikini bottom, doing a mini striptease, then grabs two of the diapers out of the diaper bag and seductively puts them on herself to demonstrate.  you stand there watching her, stunned with a stiffie.clearly if you want your swim trunks back, you'll have no choice but to join her in the water!  tsk.. tsk.. tsk.. what a "dilemma"... poor widdle diaper boy!  will you be able to resist making creamie diapers as she sweetly teases and humiliates you ? only one way to find out!enjoy! xo includes:  diaper lover, age regression, adult diaperwith:  clairemore from domination for your own good: ab step-mommie and eden diaper and encourage you to mess your diaper at portrait studio tailgate party diapering! diapered on game day by stepmommy katherine as stepsister shelley & her friend claire watches on and helps! naughty nite nite with step-mommy ]]> Wed 31 Dec 2025 12:17:19 +0200 https://pornmeka.com/videos/1501044/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-wmv/ https://pornmeka.com/videos/1420233/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-720p/
Click for hd version **top #34 c4s video- #1 in diaper discipline**   if you liked the meet the babysitter series, but ready for a playful/humiliating twist, you’ll get a kick out of part 7! your stepmommie katherine adores looking after you, but as she’s done in the past, when she has things to do, she surprises you with a special treat by periodically bringing in a new babysitter.   this time, it’s shy and pretty college girl, claire.   you’re a little extra nervous because even though you’ve had a crush on her forever, you have heard rumors she has very creative ways to deal with dorky, pathetic, diaper wearing wusses like yourself.      stepmommie katherine shows claire how to put you into double diapers and your swim trunks on over them to prepare you for swimming with her, then leaves for work.  you are really nervous as you suspect claire will quietly tell all the neighbors if you don’t do exactly as she says, so you try to be really good.  claire brings you to the pool and attempts to take you to swim.  you get embarrassed as you’ve always been shy about getting into the pool since you are diapered- especially with a pretty girl like her.     claire sweetly teases you about your shyness, tells you to stop being a big baby and tries to coax you to get into the pool.   you still hesitate, so in playful frustration claire makes you a deal:  "since you're double diapered, she'll double diaper herself to show you if she can get in the pool with diapers on, you can do it too”.  she proceeds to slide off her bikini bottom, doing a mini striptease, then grabs two of the diapers out of the diaper bag and seductively puts them on herself to demonstrate.  you stand there watching her, stunned with a stiffie, yet still hesitant to get in the pool, so she takes it a step further.   she giggles and teases you even more, pulling off your swim trunks, which completely exposes your double diapers, then with a huge smile and your swim trunks in her hand, she runs towards the pool for you to chase her, throwing your swim trunks into the pool, then gets in the pool herself while you watch in awe.     clearly if you want your swim trunks back, you'll have no choice but to join her in the water!  tsk.. tsk.. tsk.. what a "dilemma"... poor widdle diaper boy!   not realizing what’s going to happen, as she moves around in the water teasing you, her double diapers begin to swell with water and gets bigger and bigger by the second.    as they swell up to the max in the pool, they begin to lock on tightly to her beautiful voluptuous booty.    the padding has become really tight and swollen around her female parts.  she begins to massage her huge, soaked diapers making them even more soggy and wet.  she quickly finds out just how pleasurable diapers can be when they are swollen to the max like this and ready to burst.   surely this can’t be happening.. oh, but it is.. she then pulls you into the pool, up close to her breast and begins to cuddle and hold you like a baby in the water, teasing you like crazy, as your double diapers are now completely soaked too.  you get your courage up and boldly try to put your hand on her breast to begin to nurse as your little wee wee continues to grow.   you feel like you are about to burst right through your diaper and she notices.  she puts her hand down your swim trunks & feels the front of your diaper for a “diaper check”.   there’s no hiding your stiffy and she chastises you for it – how embarrassing!      she whispers playfully for you to be a good boy, step back out of the pool and to take care of your little “issue”.   being the wuss that you are, instead of making stickies, you uncontrollably mess yourself.  omg!  you’re hoping she won’t notice the smell, but there’s no way to hide this.  oops! even more embarrassing, once claire diaper checks you and realizes what a stinky mess you’ve made, she encourages you to “get the rest of it out” and offers up some of her own special “assistance”.  she slips out of the two wet/used diapers she was wearing, wringing both of them out over you, then playfully puts them over your mouth.   she notices you staring at her private parts, then changes back into her bathing suit bottom.   since you gave her such a hard time about getting into the pool, she makes you sit in your swollen, double messy diapers and encourages you to hump them.  she takes pics to show her friends, then decides to invite them over as she has her way with you as her entertainment.   will you be able to resist making creamie diapers as she sweetly teases and humiliates you ? only one way to find out! ************************************************************************** like the others in the "meet the babysitter" series, this video is shot pov style, so you are fully pulled into our world, just as if you are there and can envision yourself in his place!  it is jam packed with captivating goodies from beginning to end.   enjoy! xo ******************************************************************************* love this video? check out the entire series! meet your new babysitter- part 1 / schoolgirl twiggsy meet your new babysitter- part 2 / aunt megan meet your new babysitter- part 3 / cheerleader allison  meet your new babysitter - part 4 / public diapering & sissification  meet your new babysitter - part 5 / girl next door mia! meet your new babysitter - part 6 / babysitter madison   ]]> Fri 14 Nov 2025 11:36:03 +0200 https://pornmeka.com/videos/1420233/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-720p/ https://pornmeka.com/videos/1378174/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-mp4/
Click here for full scene **top #34 c4s video- #1 in diaper discipline**   if you liked the meet the babysitter series, but ready for a playful/humiliating twist, you’ll get a kick out of part 7! your stepmommie katherine adores looking after you, but as she’s done in the past, when she has things to do, she surprises you with a special treat by periodically bringing in a new babysitter.   this time, it’s shy and pretty college girl, claire.   you’re a little extra nervous because even though you’ve had a crush on her forever, you have heard rumors she has very creative ways to deal with dorky, pathetic, diaper wearing wusses like yourself.      stepmommie katherine shows claire how to put you into double diapers and your swim trunks on over them to prepare you for swimming with her, then leaves for work.  you are really nervous as you suspect claire will quietly tell all the neighbors if you don’t do exactly as she says, so you try to be really good.  claire brings you to the pool and attempts to take you to swim.  you get embarrassed as you’ve always been shy about getting into the pool since you are diapered- especially with a pretty girl like her.     claire sweetly teases you about your shyness, tells you to stop being a big baby and tries to coax you to get into the pool.   you still hesitate, so in playful frustration claire makes you a deal:  "since you're double diapered, she'll double diaper herself to show you if she can get in the pool with diapers on, you can do it too”.  she proceeds to slide off her bikini bottom, doing a mini striptease, then grabs two of the diapers out of the diaper bag and seductively puts them on herself to demonstrate.  you stand there watching her, stunned with a stiffie, yet still hesitant to get in the pool, so she takes it a step further.   she giggles and teases you even more, pulling off your swim trunks, which completely exposes your double diapers, then with a huge smile and your swim trunks in her hand, she runs towards the pool for you to chase her, throwing your swim trunks into the pool, then gets in the pool herself while you watch in awe.     clearly if you want your swim trunks back, you'll have no choice but to join her in the water!  tsk.. tsk.. tsk.. what a "dilemma"... poor widdle diaper boy!   not realizing what’s going to happen, as she moves around in the water teasing you, her double diapers begin to swell with water and gets bigger and bigger by the second.    as they swell up to the max in the pool, they begin to lock on tightly to her beautiful voluptuous booty.    the padding has become really tight and swollen around her female parts.  she begins to massage her huge, soaked diapers making them even more soggy and wet.  she quickly finds out just how pleasurable diapers can be when they are swollen to the max like this and ready to burst.   surely this can’t be happening.. oh, but it is.. she then pulls you into the pool, up close to her breast and begins to cuddle and hold you like a baby in the water, teasing you like crazy, as your double diapers are now completely soaked too.  you get your courage up and boldly try to put your hand on her breast to begin to nurse as your little wee wee continues to grow.   you feel like you are about to burst right through your diaper and she notices.  she puts her hand down your swim trunks & feels the front of your diaper for a “diaper check”.   there’s no hiding your stiffy and she chastises you for it – how embarrassing!      she whispers playfully for you to be a good boy, step back out of the pool and to take care of your little “issue”.   being the wuss that you are, instead of making stickies, you uncontrollably mess yourself.  omg!  you’re hoping she won’t notice the smell, but there’s no way to hide this.  oops! even more embarrassing, once claire diaper checks you and realizes what a stinky mess you’ve made, she encourages you to “get the rest of it out” and offers up some of her own special “assistance”.  she slips out of the two wet/used diapers she was wearing, wringing both of them out over you, then playfully puts them over your mouth.   she notices you staring at her private parts, then changes back into her bathing suit bottom.   since you gave her such a hard time about getting into the pool, she makes you sit in your swollen, double messy diapers and encourages you to hump them.  she takes pics to show her friends, then decides to invite them over as she has her way with you as her entertainment.   will you be able to resist making creamie diapers as she sweetly teases and humiliates you ? only one way to find out! ************************************************************************** like the others in the "meet the babysitter" series, this video is shot pov style, so you are fully pulled into our world, just as if you are there and can envision yourself in his place!  it is jam packed with captivating goodies from beginning to end.   enjoy! xo ******************************************************************************* love this video? check out the entire series! meet your new babysitter- part 1 / schoolgirl twiggsy meet your new babysitter- part 2 / aunt megan meet your new babysitter- part 3 / cheerleader allison  meet your new babysitter - part 4 / public diapering & sissification  meet your new babysitter - part 5 / girl next door mia! meet your new babysitter - part 6 / babysitter madison   ]]> Tue 21 Oct 2025 11:45:17 +0200 https://pornmeka.com/videos/1378174/meet-your-new-babysitter-part-7-double-diapered-swimming-surprise-with-shy-and-pretty-babysitter-claire-mp4/ https://pornmeka.com/videos/1306975/step-mommy-s-boy-becomes-a-diapered-sissy-cheerleader-at-the-football-stadium-720p/
Click for hd versiontoday is the day of the school football game.  you don't want anyone to hear you crinkling around in a diaper, so you've promised step-mommy you will be good so you can wear your big boy underwear.   once you arrive to the stadium, you drink a bunch of soda and really need to go pee, but the rest room is soooo far away.  and.. you are so excited by all the pretty cheerleaders and the panties you stole earlier from the girl's locker room, that.. oh no! you.. just.. can't.. hold it.. and have wet yourself.     you were so embarrassed as everyone there saw your big, wet pee pee spot, including the pretty female, school counselor- who calls your step-mom to come up to the stadium before she goes to work. step-mommy arrives and scolds you soundly for making such a big mess.   since you are acting like a baby she has to treat you like one.   like it or not, (yikes!) you're going into diapers and plastic pants right there in front of everyone.   as step-mom is pulling off your soaking wet pee pee shorts, who should walk up but (gasp!) super cute, cheerleader allison and her friend, busty cheerleader samsara.  allison had told samsara all about the time she babysat you before and what a big dorky, pathetic, diaper wearing wuss you are- but samsara never saw it for herself up close and personal-  until now.    they say hello, then watch and giggle as step-mommy starts to give you a binkie and put you in a diaper.   then, uh oh!  the panties you stole from the girl’s locker room accidentally fell out of your shorts in front of step-mommy and the girls.  step-mommy confronts you about it and samsara immediately recognizes them as hers.   as you lay there completely exposed in front of everyone, step-mommy gives you swats and makes you apologize for stealing the panties.     afterwards, the girls help step-mommy put you in your diapee as step-mommy notices she is about to be late for work, so allison offers to babysit you while her friend samsara helps.     step-mommy agrees and leaves you and your diaper bag with them.  this is a dream come true, until.. dear god.. step-mom leaves.  you quickly find out they have ulterior motives and are both going to extreme measures to teach you a lesson you will never forget.  they are going to make you into a diapered sissy cheerleader!    the girls giggle as they look through the diaper bag step-mommy has thoughtfully packed and left with them.   as you beg and plead for them to stop, they tease you unmercifully as they pull out your ba ba and pour out the milk.  then while no one is looking, allison  (omg!) spreads her legs, and makes you a “very special bottle”. you are so embarrassed but turned on at the same time.  then, samsara takes the ruffled panties you stole from her and puts them on you, over your plastic pants and diapee.   allison yanks the panties & plastic pants down, grabs a sharpie marker and writes "diaper wuss" for all the cheerleading squad to see as your dicklet continues to grow harder and harder.  then, they hold you still as you kick and squirm while allison shaves your legs as samsara watches on and laughs.  they further sissify you by applying makeup and putting you into an extra cheerleading outfit they had on hand.  allison had a wig with pigtails from drama class, so she makes you wear it.  she even slips sparkly cheerleading sneakers on your feet.  you are the most embarrassed  you've ever been in your life, but somehow your dicklet is now so hard it is sticking up through the cheerleading outfit, layers of ruffles, plastic pants and diapees.   they laugh and make you get rid of your sissy cummies right there in front of them, then hand you pom poms, and take you with them to show you off to the rest of the cheerleading squad!   a diapered sissification experience you will never be able to forget! see how it all unfolds! ]]> Wed 10 Sep 2025 12:56:18 +0200 https://pornmeka.com/videos/1306975/step-mommy-s-boy-becomes-a-diapered-sissy-cheerleader-at-the-football-stadium-720p/ https://pornmeka.com/videos/1219068/step-mommy-s-boy-becomes-a-diapered-sissy-cheerleader-at-the-football-stadium/
Today is the day of the school football game.  you don't want anyone to hear you crinkling around in a diaper, so you've promised step-mommy you will be good so you can wear your big boy underwear.   once you arrive to the stadium, you drink a bunch of soda and really need to go pee, but the rest room is soooo far away.  and.. you are so excited by all the pretty cheerleaders and the panties you stole earlier from the girl's locker room, that.. oh no! you.. just.. can't.. hold it.. and have wet yourself.     you were so embarrassed as everyone there saw your big, wet pee pee spot, including the pretty female, school counselor- who calls your step-mom to come up to the stadium before she goes to work. step-mommy arrives and scolds you soundly for making such a big mess.   since you are acting like a baby she has to treat you like one.   like it or not, (yikes!) you're going into diapers and plastic pants right there in front of everyone.   as step-mom is pulling off your soaking wet pee pee shorts, who should walk up but (gasp!) super cute, cheerleader allison and her friend, busty cheerleader samsara.  allison had told samsara all about the time she babysat you before and what a big dorky, pathetic, diaper wearing wuss you are- but samsara never saw it for herself up close and personal-  until now.    they say hello, then watch and giggle as step-mommy starts to give you a binkie and put you in a diaper.   then, uh oh!  the panties you stole from the girl’s locker room accidentally fell out of your shorts in front of step-mommy and the girls.  step-mommy confronts you about it and samsara immediately recognizes them as hers.   as you lay there completely exposed in front of everyone, step-mommy gives you swats and makes you apologize for stealing the panties.     afterwards, the girls help step-mommy put you in your diapee as step-mommy notices she is about to be late for work, so allison offers to babysit you while her friend samsara helps.     step-mommy agrees and leaves you and your diaper bag with them.  this is a dream come true, until.. dear god.. step-mom leaves.  you quickly find out they have ulterior motives and are both going to extreme measures to teach you a lesson you will never forget.  they are going to make you into a diapered sissy cheerleader!    the girls giggle as they look through the diaper bag step-mommy has thoughtfully packed and left with them.   as you beg and plead for them to stop, they tease you unmercifully as they pull out your ba ba and pour out the milk.  then while no one is looking, allison  (omg!) spreads her legs, and makes you a “very special bottle”. you are so embarrassed but turned on at the same time.  then, samsara takes the ruffled panties you stole from her and puts them on you, over your plastic pants and diapee.   allison yanks the panties & plastic pants down, grabs a sharpie marker and writes "diaper wuss" for all the cheerleading squad to see as your dicklet continues to grow harder and harder.  then, they hold you still as you kick and squirm while allison shaves your legs as samsara watches on and laughs.  they further sissify you by applying makeup and putting you into an extra cheerleading outfit they had on hand.  allison had a wig with pigtails from drama class, so she makes you wear it.  she even slips sparkly cheerleading sneakers on your feet.  you are the most embarrassed  you've ever been in your life, but somehow your dicklet is now so hard it is sticking up through the cheerleading outfit, layers of ruffles, plastic pants and diapees.   they laugh and make you get rid of your sissy cummies right there in front of them, then hand you pom poms, and take you with them to show you off to the rest of the cheerleading squad!   a diapered sissification experience you will never be able to forget! see how it all unfolds! ]]> Mon 21 Jul 2025 11:59:20 +0200 https://pornmeka.com/videos/1219068/step-mommy-s-boy-becomes-a-diapered-sissy-cheerleader-at-the-football-stadium/