Sissy Ideas 19 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. I think one of my favorites here is Matthew helping his mother and sister with the alterations on her friend Maddies bridesmaid dress. Maddie is out of town and the wedding is next weekend. Maddie is a tall girl, so Mathew’s sister can’t just wear her dress while her mother does the alterations. They convince Matthew to stand in for a Maddie as the dress model, as he is about her height. Of course Maddies has breasts and no bulge in the front, so Matthew has to wear a bra and tight panties, to better mimic Maddie’s natural curves. The smooth and silky stockings help the dress fall correctly against his body. While trying to be helpful, Matthew is terribly embarrassed by the whole ordeal, even though his mother and sister find it very amusing.     Saving...     Description saved I think one of my favorites here is Matthew helping his mother and sister with the alterations on her friend Maddies bridesmaid dress. Maddie is out of town and the wedding is next weekend. Maddie is a tall girl, so Mathew’s sister can’t just wear her dress while her mother does the alterations. They convince Matthew to stand in for a Maddie as the dress model, as he is about her height. Of course Maddies has breasts and no bulge in the front, so Matthew has to wear a bra and tight panties, to better mimic Maddie’s natural curves. The smooth and silky stockings help the dress fall correctly against his body. While trying to be helpful, Matthew is terribly embarrassed by the whole ordeal, even though his mother and sister find it very amusing. Gallery Categories: AI Generated Gallery Tags: sissy, sissy maid, maid, femdom, humiliation, feminization, stockings, pantyhose 10,0 (30 votes) Detailed View  /  One page All a little drunk by the end of the night, his wife’s Thursday Bunco group always liked to end the evening with some fun little game.     Saving...     Description saved All a little drunk by the end of the night, his wife’s Thursday Bunco group always liked to end the evening with some fun little game. img-0237.jpeg 1024 x 1024 < 1690 Views > They had offered him a $1000 to do the match, but it was not going anywhere near how Josh thought it would.     Saving...     Description saved They had offered him a $1000 to do the match, but it was not going anywhere near how Josh thought it would. img-0251.jpeg 1024 x 1024 < 470 Views > “I love your staff’s new uniforms Marie. They look just adorable”     Saving...     Description saved “I love your staff’s new uniforms Marie. They look just adorable” img-0312.jpeg 1024 x 1024 < 408 Views > “Don’t worry about anybody else. I think you are very brave and you look gorgeous!”     Saving...     Description saved “Don’t worry about anybody else. I think you are very brave and you look gorgeous!” img-1035.png 1024 x 1024 < 605 Views > It was Shelly’s idea. But he loved her dearly and he wanted her to be happy.     Saving...     Description saved It was Shelly’s idea. But he loved her dearly and he wanted her to be happy. img-1108.png 1024 x 1024 < 531 Views > Oh thank you Matthew! I know it’s a little strange, but Maddie is very tall like you, and with her out of town… well we need to get these alterations done on her dress before your sister’s wedding next week.     Saving...     Description saved Oh thank you Matthew! I know it’s a little strange, but Maddie is very tall like you, and with her out of town… well we need to get these alterations done on her dress before your sister’s wedding next week. img-1117.png 1024 x 1024 < 444 Views > Paula just loved parties at Michelle’s home. The food was amazing as usual, and she was always interested to see Michelle’s husband Trevor, since they completed the Callahan program.     Saving...     Description saved Paula just loved parties at Michelle’s home. The food was amazing as usual, and she was always interested to see Michelle’s husband Trevor, since they completed the Callahan program. img-1118.png 1024 x 1024 < 285 Views > Thank you for your cooperation gentlemen. As you know stockings are the requirement, and some of the staff have been wearing pantyhose, or no hosiery at all.     Saving...     Description saved Thank you for your cooperation gentlemen. As you know stockings are the requirement, and some of the staff have been wearing pantyhose, or no hosiery at all. img-9668.jpeg 1024 x 1024 < 324 Views > Mrs. Callahan frowned as she noticed the new facial hair on her personal assistant Kevin’s jawline. “That would have to go.” She thought to herself.     Saving...     Description saved Mrs. Callahan frowned as she noticed the new facial hair on her personal assistant Kevin’s jawline. “That would have to go.” She thought to herself. img-9680.jpeg 1024 x 1024 < 254 Views > “She had to be perfect for her date.” He thought to himself, as he gently combed his wife’s onyx hair.     Saving...     Description saved “She had to be perfect for her date.” He thought to himself, as he gently combed his wife’s onyx hair. img-9691.jpeg 1024 x 1024 < 282 Views > “Your house is immaculate Kendra! How do you find the time to keep up with it all?”     Saving...     Description saved “Your house is immaculate Kendra! How do you find the time to keep up with it all?” img-9707.jpeg 1024 x 1024 < 252 Views > “Pink again this week Ma’am? Or maybe a light robin’s egg blue for spring.”     Saving...     Description saved “Pink again this week Ma’am? Or maybe a light robin’s egg blue for spring.” img-9787.jpeg 1024 x 1024 < 296 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/13997854 Or generate html/bbcode here Report this gallery