A Sissy Sleepover Uploaded by ALilBroken Profile | Galleries | Videos | Favorites | Fanbase | Clubs | Comments | Blog | Chat Add a description of the contents of your gallery, so it will be more visible for other users. Remember that you can also add descriptions to each image. Caleb’s parents have gone away for the weekend, but his idea of an easy couple of days off from chores is about to come to an abrupt end. His sister Nicole found out about his traffic ticket that he had been hiding from his parents, and she has other plans for Caleb. Caleb is going to spend the weekend as Nicole’s personal sissy maid. But nothing is ever that simple for the poor guys in my little world. After forcing Caleb to crossdress in a pink maids dress and pantyhose, Nicole invites her two best friends Ally and Candice over for the weekend, and together, they are going to make sure that Caleb has a weekend that he never forgets. And as Caleb is soon to find out, his life as a sissy maid may be just beginning. Please enjoy this story of feminization, humiliation, servitude, torment and even a little forced bi for our poor little sissy boi Caleb.     Saving...     Description saved Caleb’s parents have gone away for the weekend, but his idea of an easy couple of days off from chores is about to come to an abrupt end. His sister Nicole found out about his traffic ticket that he had been hiding from his parents, and she has other plans for Caleb. Caleb is going to spend the weekend as Nicole’s personal sissy maid. But nothing is ever that simple for the poor guys in my little world. After forcing Caleb to crossdress in a pink maids dress and pantyhose, Nicole invites her two best friends Ally and Candice over for the weekend, and together, they are going to make sure that Caleb has a weekend that he never forgets. And as Caleb is soon to find out, his life as a sissy maid may be just beginning. Please enjoy this story of feminization, humiliation, servitude, torment and even a little forced bi for our poor little sissy boi Caleb. Gallery Categories: Fetish, CD / TV, Crossdressing Gallery Tags: sissy, sissy maid, feminization, crossdressing, humiliation, pantyhose, stockings, femdom 10,0 (40 votes) Detailed View  /  One page Their parents had barely put the suitcases in the car when Nicole confronted her brother Caleb in the living room with his traffic ticket. “Last time you left everything to me, but this weekend, you’re going to do all the chores!”     Saving...     Description saved Their parents had barely put the suitcases in the car when Nicole confronted her brother Caleb in the living room with his traffic ticket. “Last time you left everything to me, but this weekend, you’re going to do all the chores!” img-2619.png 1254 x 1254 < 295 Views > Caleb followed her to her room, trying to talk some sense into her. Instead, she surprised him saying, “ Not only are you doing my chores, but if you don’t wear the dress, I’m going to tell Mom and Dad about the traffic ticket you’ve been hiding from them     Saving...     Description saved Caleb followed her to her room, trying to talk some sense into her. Instead, she surprised him saying, “ Not only are you doing my chores, but if you don’t wear the dress, I’m going to tell Mom and Dad about the traffic ticket you’ve been hiding from them img-2620.png 1254 x 1254 < 113 Views > Caleb weighed his options and quickly decided to put on the dress and do what his sister said. Nicole basked in her victory as she stood back and took a video of her brother dressing in his new sissy outfit.     Saving...     Description saved Caleb weighed his options and quickly decided to put on the dress and do what his sister said. Nicole basked in her victory as she stood back and took a video of her brother dressing in his new sissy outfit. img-2621.png 1254 x 1254 < 167 Views > Caleb followed Nicole downstairs, where she presented him with a list of chores that she expected him to complete before their parents returned on Sunday.     Saving...     Description saved Caleb followed Nicole downstairs, where she presented him with a list of chores that she expected him to complete before their parents returned on Sunday. img-2622.png 1254 x 1254 < 149 Views > Over the next several hours, Caleb worked diligently in his humiliating maid’s dress and hot itchy pantyhose, as Nicole lounged, watching television and talking to her friends on the phone.     Saving...     Description saved Over the next several hours, Caleb worked diligently in his humiliating maid’s dress and hot itchy pantyhose, as Nicole lounged, watching television and talking to her friends on the phone. img-2623.png 1254 x 1254 < 45 Views > Engrossed in his cleaning, Caleb barely heard the doorbell ring when he looked up and saw his sister’s two best friends Ally and Candace standing at the front door, laughing hysterically.     Saving...     Description saved Engrossed in his cleaning, Caleb barely heard the doorbell ring when he looked up and saw his sister’s two best friends Ally and Candace standing at the front door, laughing hysterically. img-2624.png 1254 x 1254 < 63 Views > The girls quickly changed into their bathing suits, and soon Caleb found himself bringing them drinks and whatever else they wanted, poolside.     Saving...     Description saved The girls quickly changed into their bathing suits, and soon Caleb found himself bringing them drinks and whatever else they wanted, poolside. img-2625.png 1254 x 1254 < 45 Views > After they were done swimming, the girls all gave Caleb their bathing suits to rinse out. Ally took particular pleasure in dropping her towel a bit, flashing an already flustered Caleb with her perfect breasts.     Saving...     Description saved After they were done swimming, the girls all gave Caleb their bathing suits to rinse out. Ally took particular pleasure in dropping her towel a bit, flashing an already flustered Caleb with her perfect breasts. img-2626.png 1024 x 1024 < 51 Views > The girls went to Nicole’s bedroom to finish getting ready. Ally insisted that Caleb paint her toenails, and she made sure to spread her legs from time to time, tempting him with glimpses of her neatly trimmed pussy.     Saving...     Description saved The girls went to Nicole’s bedroom to finish getting ready. Ally insisted that Caleb paint her toenails, and she made sure to spread her legs from time to time, tempting him with glimpses of her neatly trimmed pussy. img-2627.png 1254 x 1254 < 83 Views > Once dressed, Ally made Caleb take off his shoes and bend over the coffee table. To the delight of the other girls, she gave his several hard swats on his bottom for every time he had looked at her naked body, turning his nylon covered ass a crimson red.     Saving...     Description saved Once dressed, Ally made Caleb take off his shoes and bend over the coffee table. To the delight of the other girls, she gave his several hard swats on his bottom for every time he had looked at her naked body, turning his nylon covered ass a crimson red. img-2628.png 1024 x 1024 < 77 Views > Not content with the spankings, Ally took Caleb outside where everyone in the neighborhood could see him, and made him wash her car.     Saving...     Description saved Not content with the spankings, Ally took Caleb outside where everyone in the neighborhood could see him, and made him wash her car. img-2629.png 1254 x 1254 < 40 Views > Once back inside, Nicole told Caleb that he needed to calm his hormones, and if he didn’t want another spanking, he had to jerk off in front of everyone. She showed him pictures of guys with huge dicks and to their shock, Caleb came almost immediately.     Saving...     Description saved Once back inside, Nicole told Caleb that he needed to calm his hormones, and if he didn’t want another spanking, he had to jerk off in front of everyone. She showed him pictures of guys with huge dicks and to their shock, Caleb came almost immediately. img-2630.png 1024 x 1024 < 51 Views > The girls ordered pizza, and watched in delight as Caleb answered the door and payed the delivery guy. Nicole surprised everyone when she invited the delivery guy in for a “special” tip.     Saving...     Description saved The girls ordered pizza, and watched in delight as Caleb answered the door and payed the delivery guy. Nicole surprised everyone when she invited the delivery guy in for a “special” tip. img-2631.png 1254 x 1254 < 45 Views > They all expected that Caleb might half heartedly suck the delivery guy’s dick for a second or two at most and be done with it, but they we’re stunned when he came huge in poor Caleb’s mouth just 10 seconds later.     Saving...     Description saved They all expected that Caleb might half heartedly suck the delivery guy’s dick for a second or two at most and be done with it, but they we’re stunned when he came huge in poor Caleb’s mouth just 10 seconds later. img-2632.png 1024 x 1024 < 95 Views > Candace felt bad for Caleb, and tried to make him feel better after he rushed to the bathroom to brush the salty, bitter cum out of his mouth in disgust.     Saving...     Description saved Candace felt bad for Caleb, and tried to make him feel better after he rushed to the bathroom to brush the salty, bitter cum out of his mouth in disgust. img-2633.png 1254 x 1254 < 48 Views > Each girl took one of the three beds in the house, leaving Caleb to sleep on the hard cold floor of his own bedroom that night.     Saving...     Description saved Each girl took one of the three beds in the house, leaving Caleb to sleep on the hard cold floor of his own bedroom that night. img-2634.png 1254 x 1254 < 52 Views > The next morning, exhausted from a restless sleep on the hard floor, Caleb made the girls breakfast.     Saving...     Description saved The next morning, exhausted from a restless sleep on the hard floor, Caleb made the girls breakfast. img-2635.png 1254 x 1254 < 44 Views > Caleb brought the girls fresh towels as they showered, careful not to look too closely as Ally peeked around the curtain with her exposed breasts, as he did not want any more spankings.     Saving...     Description saved Caleb brought the girls fresh towels as they showered, careful not to look too closely as Ally peeked around the curtain with her exposed breasts, as he did not want any more spankings. img-2650.png 1024 x 1024 < 54 Views > Before they left, Ally and Candace both made a point to tell Caleb that he was a really good sport this weekend, and thank him for his exceptional service.     Saving...     Description saved Before they left, Ally and Candace both made a point to tell Caleb that he was a really good sport this weekend, and thank him for his exceptional service. img-2651.png 1254 x 1254 < 78 Views > But then without warning, Ally kneed Caleb hard in the balls, laughing as she told him that she just wanted to be sure that such a little sissy bitch of a guy even had a pair.     Saving...     Description saved But then without warning, Ally kneed Caleb hard in the balls, laughing as she told him that she just wanted to be sure that such a little sissy bitch of a guy even had a pair. img-2652.png 1254 x 1254 < 75 Views > Exhausted and overwhelmed, Caleb barely heard his parents when they arrived home, He sprinted up the stairs to his bedroom so they wouldn’t see him dressed this way.     Saving...     Description saved Exhausted and overwhelmed, Caleb barely heard his parents when they arrived home, He sprinted up the stairs to his bedroom so they wouldn’t see him dressed this way. img-2653.png 1254 x 1254 < 60 Views > When he returned downstairs to greet his parents, Caleb saw his father holding his traffic ticket and he heard Nicole telling them, “And then we ordered a pizza for dinner.” As she showed them a video on her cellphone.     Saving...     Description saved When he returned downstairs to greet his parents, Caleb saw his father holding his traffic ticket and he heard Nicole telling them, “And then we ordered a pizza for dinner.” As she showed them a video on her cellphone. img-2654.png 1254 x 1254 < 70 Views > Caleb’s parents, rightfully upset, insisted that he show them the maid’s dress that he had been wearing all weekend.     Saving...     Description saved Caleb’s parents, rightfully upset, insisted that he show them the maid’s dress that he had been wearing all weekend. img-2655.png 1024 x 1024 < 94 Views > As a further punishment for the traffic ticket, for the next month, Caleb’s parents made him do all of the chores in the house on Saturday and Sunday. Dressed appropriately of course.     Saving...     Description saved As a further punishment for the traffic ticket, for the next month, Caleb’s parents made him do all of the chores in the house on Saturday and Sunday. Dressed appropriately of course. img-2656.png 1254 x 1254 < 93 Views > Users who added this gallery You have to login in order to favorite this gallery Send this link to a friend To link to this gallery use : https://www.imagefap.com/gallery/14297481 Or generate html/bbcode here Report this gallery