The Maids Sissy Maid 2 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. Here is what happens when LongstockingsMe tells me in the comments that he thinks Brian’s wife Karen is very pretty, and asks me what I think might happen if she found out about her husband dressing up like a sissy maid. So with that challenge, we revisit Brian O’Neil and his housekeeper Paola. Brian is still dressing up like a maid on Thursdays when he works from home, but his secret is not for long. Brian’s wife Karen discovers his hobby and is none too happy about it. Furious, Karen devises a plan to profit off of her husband’s little kink, and soon Brian finds himself in a much more humiliating situation than before. Please enjoy this little story from my broken mind. As always, it involves dominant femdom women taking control of submissive beta bois, and humiliating them through forced feminization for the lady’s own benefit and amusement. I like my male characters to present as obviously male and not passable female crossdressers, as I think it is much more humiliating for them that way. And as always, my boys wear pantyhose or stockings because I like them that way :) Happy fapping my friends, and I hope these help someone cum today.     Saving...     Description saved Here is what happens when LongstockingsMe tells me in the comments that he thinks Brian’s wife Karen is very pretty, and asks me what I think might happen if she found out about her husband dressing up like a sissy maid. So with that challenge, we revisit Brian O’Neil and his housekeeper Paola. Brian is still dressing up like a maid on Thursdays when he works from home, but his secret is not for long. Brian’s wife Karen discovers his hobby and is none too happy about it. Furious, Karen devises a plan to profit off of her husband’s little kink, and soon Brian finds himself in a much more humiliating situation than before. Please enjoy this little story from my broken mind. As always, it involves dominant femdom women taking control of submissive beta bois, and humiliating them through forced feminization for the lady’s own benefit and amusement. I like my male characters to present as obviously male and not passable female crossdressers, as I think it is much more humiliating for them that way. And as always, my boys wear pantyhose or stockings because I like them that way :) Happy fapping my friends, and I hope these help someone cum today. Gallery Categories: AI Generated Gallery Tags: sissy, sissy maid, maid, humiliation, feminization, crossdressing, pantyhose, femdom 7,4 (62 votes) Detailed View  /  One page “Here it was again.” Thought Karen, as she went to her lingerie drawer Thursday after work. “Someone’s been in here. Could it be Paola?” She thought puzzled. “That would be weird.”     Saving...     Description saved “Here it was again.” Thought Karen, as she went to her lingerie drawer Thursday after work. “Someone’s been in here. Could it be Paola?” She thought puzzled. “That would be weird.” img-3412.png 1024 x 1024 < 924 Views > That weekend, Karen decided to set up a nanny cam in the bedroom to try to get to the bottom of her little mystery.     Saving...     Description saved That weekend, Karen decided to set up a nanny cam in the bedroom to try to get to the bottom of her little mystery. img-3413.png 1254 x 1254 < 224 Views > The next Thursday, her cell phone buzzed indicating activity on the cam. Karen pulled up the camera on her work computer and was stunned by what she saw. Her husband Brian was putting laundry away in the bedroom, but he was dressed as a maid!     Saving...     Description saved The next Thursday, her cell phone buzzed indicating activity on the cam. Karen pulled up the camera on her work computer and was stunned by what she saw. Her husband Brian was putting laundry away in the bedroom, but he was dressed as a maid! img-3418.png 1254 x 1254 < 296 Views > Furious, Karen raced home, only to find Brian still dressed like a sissy maid and vacuuming the living room, while Paola lounged on the couch with a beer.     Saving...     Description saved Furious, Karen raced home, only to find Brian still dressed like a sissy maid and vacuuming the living room, while Paola lounged on the couch with a beer. img-3419.png 1254 x 1254 < 320 Views > Stunned by his wife's sudden arrival, Brian quickly pointed to Paola. “She made me… I mean… It was her idea!” He stammered. Karen turned to Paola furious.     Saving...     Description saved Stunned by his wife's sudden arrival, Brian quickly pointed to Paola. “She made me… I mean… It was her idea!” He stammered. Karen turned to Paola furious. img-3416.png 1254 x 1254 < 144 Views > Paola quickly took out her cellphone. Brian hung his head in utter humiliation as Paola showed Karen video after video of him happily cleaning the house in his ridiculous costume.     Saving...     Description saved Paola quickly took out her cellphone. Brian hung his head in utter humiliation as Paola showed Karen video after video of him happily cleaning the house in his ridiculous costume. img-3422.png 1254 x 1254 < 117 Views > Unsure what to do next, Karen stormed out of the house, leaving Brian and Paola standing together in stunned silence.     Saving...     Description saved Unsure what to do next, Karen stormed out of the house, leaving Brian and Paola standing together in stunned silence. img-3423.png 1254 x 1254 < 107 Views > A few hours later, Karen returned home. She was carrying shopping bags and still very angry. Brian tried to explain, but she just pointed to the hallway and said, “Bedroom…Now!”     Saving...     Description saved A few hours later, Karen returned home. She was carrying shopping bags and still very angry. Brian tried to explain, but she just pointed to the hallway and said, “Bedroom…Now!” img-3436.png 1254 x 1254 < 108 Views > Karen reached into a shopping bag on the bed and pulled out a pink maid’s uniform. “If you are going to dress like a maid, Brian.” She growled. “You are going to have a proper uniform.”     Saving...     Description saved Karen reached into a shopping bag on the bed and pulled out a pink maid’s uniform. “If you are going to dress like a maid, Brian.” She growled. “You are going to have a proper uniform.” img-3437.png 1024 x 1024 < 99 Views > Brian quietly went through the shopping bags and put on the lingerie that Karen had bought for him. Karen handed him a shoebox. “Paola was kind enough to let you wear flats.” She said coldly.” My maids wear heels.”     Saving...     Description saved Brian quietly went through the shopping bags and put on the lingerie that Karen had bought for him. Karen handed him a shoebox. “Paola was kind enough to let you wear flats.” She said coldly.” My maids wear heels.” img-3446.png 1024 x 1024 < 136 Views > As Brian finished dressing, he was surprised to hear Karen call Paola and ask her to return to the house.     Saving...     Description saved As Brian finished dressing, he was surprised to hear Karen call Paola and ask her to return to the house. img-3447.png 1024 x 1024 < 147 Views > Sensing her discomfort, Karen smiled and assured Paola that there were no hard feelings. In fact, she told the girl, she had a business proposition to discuss with her.     Saving...     Description saved Sensing her discomfort, Karen smiled and assured Paola that there were no hard feelings. In fact, she told the girl, she had a business proposition to discuss with her. img-3448.png 1254 x 1254 < 143 Views > Karen went over her idea for a sissy maid house cleaning service with Paola, while Brian listened is as best he could and brought the two women drinks.     Saving...     Description saved Karen went over her idea for a sissy maid house cleaning service with Paola, while Brian listened is as best he could and brought the two women drinks. img-3455.png 1024 x 1024 < 98 Views > With Paola happily on board, Karen informed Brian that he would in fact be the sissy maid they would be hiring out to clients, and Paola was going to be his new boss.     Saving...     Description saved With Paola happily on board, Karen informed Brian that he would in fact be the sissy maid they would be hiring out to clients, and Paola was going to be his new boss. img-3490.png 1254 x 1254 < 108 Views > A few weeks later, as Paola drove Brian to his first cleaning job, he winced as he saw the large billboards that Karen had put up all over town to advertise the business. There he was in his maid’s dress, for the whole town to see.     Saving...     Description saved A few weeks later, as Paola drove Brian to his first cleaning job, he winced as he saw the large billboards that Karen had put up all over town to advertise the business. There he was in his maid’s dress, for the whole town to see. img-3491.png 1254 x 1254 < 103 Views > Brian found that not many suburban housewives were interested in a sissy maid to help around the house, but plenty of older men were.     Saving...     Description saved Brian found that not many suburban housewives were interested in a sissy maid to help around the house, but plenty of older men were. img-3492.png 1254 x 1254 < 124 Views > Brian also found out that most of his clients really didn’t care if their house was clean or not, but Karen and Paola had negotiated extra payment from them for additional services that Brian was expected to perform.     Saving...     Description saved Brian also found out that most of his clients really didn’t care if their house was clean or not, but Karen and Paola had negotiated extra payment from them for additional services that Brian was expected to perform. img-3493.png 1254 x 1254 < 98 Views > Most of Brain’s clients were happy with a simple handjob or blowjob, but a few of them had specific kinks that they used Brian to help them act out. One guy in particular loved cumming all over Brian’s nylon covered feet.     Saving...     Description saved Most of Brain’s clients were happy with a simple handjob or blowjob, but a few of them had specific kinks that they used Brian to help them act out. One guy in particular loved cumming all over Brian’s nylon covered feet. img-3494.png 1254 x 1254 < 123 Views > Brian learned that his old high school gym coach Mr. Allen really liked raw anal, and damn it hurt every time. The old guy was hung like a horse and Brian leaked cum from his ass for hours afterwards.     Saving...     Description saved Brian learned that his old high school gym coach Mr. Allen really liked raw anal, and damn it hurt every time. The old guy was hung like a horse and Brian leaked cum from his ass for hours afterwards. img-3495.png 1254 x 1254 < 164 Views > Brian returned home one Thursday night to find Paola and Karen discussing expanding his services to 5 days a week. And he could do it now, since his old job fired him immediately when they found out he was working as a sissymaid on his telecommute day.     Saving...     Description saved Brian returned home one Thursday night to find Paola and Karen discussing expanding his services to 5 days a week. And he could do it now, since his old job fired him immediately when they found out he was working as a sissymaid on his telecommute day. img-3496.png 1254 x 1254 < 161 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/14387093 Or generate html/bbcode here Report this gallery