Sissy ideas 40 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. Please enjoy another gallery from my broken mind, of sissies, sissy maids, crossdressers, fem bois, cuckolds, and generally humiliated submissive young men, feminized by dominant femdom women for their amusement and benefit. I even have a couple of poor guys wearing diapers in this one, as I know some of you love that! My male characters present as obviously male, as I feel that is so much more humiliating in these situations, than a guy who can convincingly pass as a woman. And as always, my male characters are usually wearing pantyhose or stockings, because I have a huge fetish for it. Happy fapping friends! I hope these help someone cum today :)     Saving...     Description saved Please enjoy another gallery from my broken mind, of sissies, sissy maids, crossdressers, fem bois, cuckolds, and generally humiliated submissive young men, feminized by dominant femdom women for their amusement and benefit. I even have a couple of poor guys wearing diapers in this one, as I know some of you love that! My male characters present as obviously male, as I feel that is so much more humiliating in these situations, than a guy who can convincingly pass as a woman. And as always, my male characters are usually wearing pantyhose or stockings, because I have a huge fetish for it. Happy fapping friends! I hope these help someone cum today :) Gallery Categories: Fetish, CD / TV, Crossdressing Gallery Tags: sissy, sissy maid, feminization, humiliation, crossdress, femdom, cuckold, pantyhose, stockings 9,9 (65 votes) Detailed View  /  One page As Carol cheerfully explained the powerful role the bra had in the Callahan husband training program to the women in the room, Dan carefully closed the clasp on the front of the soft white garment, and quietly reflected on how fast his life had changed.     Saving...     Description saved As Carol cheerfully explained the powerful role the bra had in the Callahan husband training program to the women in the room, Dan carefully closed the clasp on the front of the soft white garment, and quietly reflected on how fast his life had changed. img-2496.png 1254 x 1254 < 786 Views > “Nope. Thats just perfect!” Laughed Ashley, as she looked at her brother Mark holding the pink bikini top, its outline now seared onto his chest for the summer. “You can leave it off now, if you want.”     Saving...     Description saved “Nope. Thats just perfect!” Laughed Ashley, as she looked at her brother Mark holding the pink bikini top, its outline now seared onto his chest for the summer. “You can leave it off now, if you want.” img-2669.png 1024 x 1024 < 350 Views > With no comparable boy’s school nearby, and his parents wanting him to have the best education possible, they sent Peter to the Callahan Preperatroy School for Girls. Of course that meant a certain amount of hazing from the other students.     Saving...     Description saved With no comparable boy’s school nearby, and his parents wanting him to have the best education possible, they sent Peter to the Callahan Preperatroy School for Girls. Of course that meant a certain amount of hazing from the other students. img-2678.png 1024 x 1024 < 358 Views > It was their ritual. Well her ritual anyway. After her dates left, Kevin had to drink the glass in order to retrieve Mari’s wedding ring and symbolically reclaim her as his wife. Then he could take off the dress.     Saving...     Description saved It was their ritual. Well her ritual anyway. After her dates left, Kevin had to drink the glass in order to retrieve Mari’s wedding ring and symbolically reclaim her as his wife. Then he could take off the dress. img-2479.png 1254 x 1254 < 229 Views > Of course Jacquelyn was tall enough to retrieve the file for Mrs.Callahan by herself. But she got a perverse and sadistic joy from watching Scott do it.     Saving...     Description saved Of course Jacquelyn was tall enough to retrieve the file for Mrs.Callahan by herself. But she got a perverse and sadistic joy from watching Scott do it. img-2477.png 1254 x 1254 < 113 Views > “Yeah. We’re staying at the hotel right over there. Do you want to come up and see my room?”     Saving...     Description saved “Yeah. We’re staying at the hotel right over there. Do you want to come up and see my room?” img-2481.png 1254 x 1254 < 163 Views > “You won’t be needing these nasty men’s boxer shorts anymore. We have something much nicer for you.”     Saving...     Description saved “You won’t be needing these nasty men’s boxer shorts anymore. We have something much nicer for you.” img-2485.png 1024 x 1024 < 168 Views > Upon his arrival at his aunt Maria’s villa in Spain for the summer, Marco made the terrible mistake of telling his cousin Paola that housework was a woman’s job.     Saving...     Description saved Upon his arrival at his aunt Maria’s villa in Spain for the summer, Marco made the terrible mistake of telling his cousin Paola that housework was a woman’s job. img-2490.png 1254 x 1254 < 142 Views > They both fought with all their might to hold it in. Knowing that the first person to piss in their diaper had to kneel down and take the other guy’s dick in his mouth, as well as the inevitable flood that would follow.     Saving...     Description saved They both fought with all their might to hold it in. Knowing that the first person to piss in their diaper had to kneel down and take the other guy’s dick in his mouth, as well as the inevitable flood that would follow. img-2492.png 1024 x 1024 < 197 Views > “I mean it’s your marriage to command now Chelsea, but we’ve found that an initial period of feminization, even just a brief one, can really help set the groundwork for future issues as they may arise.”     Saving...     Description saved “I mean it’s your marriage to command now Chelsea, but we’ve found that an initial period of feminization, even just a brief one, can really help set the groundwork for future issues as they may arise.” img-2504.png 1254 x 1254 < 98 Views > “Are you ready to earn your deep throat and creampie badges?”     Saving...     Description saved “Are you ready to earn your deep throat and creampie badges?” img-2509.png 1254 x 1254 < 101 Views > “Nice job on your first day Paul. A couple of us are going out to a bar downtown from here. Want to join us? You’d be surprised the attention and free drinks the uniform can get you.”     Saving...     Description saved “Nice job on your first day Paul. A couple of us are going out to a bar downtown from here. Want to join us? You’d be surprised the attention and free drinks the uniform can get you.” img-2512.png 1254 x 1254 < 90 Views > Carlos wished he had considered the wind a little more when he made his panty choice this morning.     Saving...     Description saved Carlos wished he had considered the wind a little more when he made his panty choice this morning. img-2601.png 1254 x 1254 < 90 Views > What was suppose to be an exhilarating quick dash to the ice machine was quickly turning into a full blown catastrophe, after Mason realized that he accidentally left the room key on the TV stand.     Saving...     Description saved What was suppose to be an exhilarating quick dash to the ice machine was quickly turning into a full blown catastrophe, after Mason realized that he accidentally left the room key on the TV stand. img-2604.png 1024 x 1024 < 124 Views > She waited for him in the car, watching from the parking lot and laughing hysterically.     Saving...     Description saved She waited for him in the car, watching from the parking lot and laughing hysterically. img-2657.png 1254 x 1254 < 113 Views > It was a shame that she was going to have to fire him, Mrs. Callahan thought to herself. Adam was actually very good at his job, but he just wasn’t Callahan material.     Saving...     Description saved It was a shame that she was going to have to fire him, Mrs. Callahan thought to herself. Adam was actually very good at his job, but he just wasn’t Callahan material. img-2658.png 1254 x 1254 < 87 Views > No worries Cale. You are dressed in the spirit of the dress code, and these things aren’t always intuitive to a young man. Jeffery here will take you over to the Nordstrom’s and get you a proper work outfit to start.     Saving...     Description saved No worries Cale. You are dressed in the spirit of the dress code, and these things aren’t always intuitive to a young man. Jeffery here will take you over to the Nordstrom’s and get you a proper work outfit to start. img-2687.png 1254 x 1254 < 88 Views > After demonstrating the move for the class, the five women all lined up and took several turns each, practicing the kick on Will with their full force.     Saving...     Description saved After demonstrating the move for the class, the five women all lined up and took several turns each, practicing the kick on Will with their full force. img-2688.png 1254 x 1254 < 101 Views > Ally quickly stripped off his satin panties leaving him exposed. As he felt the strong hands grip his shoulders and the breeze under his dress, Mary smiled cruelly and said, “Now tell the camera how badly you want him to cum in your tight little asshole.”     Saving...     Description saved Ally quickly stripped off his satin panties leaving him exposed. As he felt the strong hands grip his shoulders and the breeze under his dress, Mary smiled cruelly and said, “Now tell the camera how badly you want him to cum in your tight little asshole.” img-2691.png 1254 x 1254 < 133 Views > As the man 10 years younger escorted his wife out of the room, Walter rushed to finish making the bed. Coffee was ready in the kitchen, but he still had to make them breakfast.     Saving...     Description saved As the man 10 years younger escorted his wife out of the room, Walter rushed to finish making the bed. Coffee was ready in the kitchen, but he still had to make them breakfast. img-2701.png 1254 x 1254 < 135 Views > Macey entered the room after a long day at work and looked over Giorgio as he waited for her in the den. She took in his contrasting muscles and his soft feminine clothing. She would start with his tongue, she thought to herself, and then see where it led     Saving...     Description saved Macey entered the room after a long day at work and looked over Giorgio as he waited for her in the den. She took in his contrasting muscles and his soft feminine clothing. She would start with his tongue, she thought to herself, and then see where it led img-2710.png 1024 x 1024 < 98 Views > Michael’s trophy wall sure had changed a lot since he left college and married Penny.     Saving...     Description saved Michael’s trophy wall sure had changed a lot since he left college and married Penny. img-2712.png 1254 x 1254 < 108 Views > “I mean it doesn’t look bad, but it’s not usually what the other men who work at Callahan go for when they shop here. Might I show you a nice cream blouse and a pencil skirt.”     Saving...     Description saved “I mean it doesn’t look bad, but it’s not usually what the other men who work at Callahan go for when they shop here. Might I show you a nice cream blouse and a pencil skirt.” img-2714.png 1254 x 1254 < 111 Views > Thank you all so much for the love and support that you have given my sissy ideas!     Saving...     Description saved Thank you all so much for the love and support that you have given my sissy ideas! img-2672.png 1254 x 1254 < 120 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/14314534 Or generate html/bbcode here Report this gallery