Wow! What a delightful selection. Impossible to choose a favorite, but what boi would want to be a boring boy when he can look so sensual? You did save the best for the end. IMHO. Who would not want such a beauty on their arm?
I cannot help but fall in love with Cover Boi Tim. And the article "When it's time to tell your family." With the suggestion to bring Mistress along sounds so helpful.
Hmm? The Sissy appears to be young, possibly in "her" early 20's. I believe the mother might be correct. The Sissy has grown out her hair to look "Cool" I would imagine? What better way for Mummy to exhibit her control and dominance in the situation than to decree a short styling, such as a severe undercut with a tight perm on top. I can imagine how vulnerable the prim Sissy just might feel when the mother's boss's Alpha Male son puts his Beefy arm around her as they walk into the "Drag" bar on their very 1st of many date-night's out.
I agree with caption #2, however one purse would never be enough. A sissy might start her collection with a wristlet, move up to a clutch, then a hobo. Eventually she will begin to carry a satchel which will hold a make-up bag, a spare pair of pantyhose, a hairbrush, panty shields , hand lotion and condoms. A sissy would never leave the house without her purse. Some sissies spend countless hours on their knees attempting to convince their Husbands to build them a shoe and purse closet to display their collection. Donna
Wow! What a delightful selection. Impossible to choose a favorite, but what boi would want to be a boring boy when he can look so sensual? You did save the best for the end. IMHO. Who would not want such a beauty on their arm?
ReplyDeleteThank you, I appreciate that, I try to arrange the lineup with some order
DeleteCover boi Toni is adorable. Id love to read his journey into how he became a sissy and introduced to men.
ReplyDeleteSame, I would also like to know...
DeleteSo many wonderful captions. Each one sparks the imagination and sends a little shiver. Thanks to those that made them happen.
ReplyDeleteYou are welcome
DeleteI cannot help but fall in love with Cover Boi Tim. And the article "When it's time to tell your family." With the suggestion to bring Mistress along sounds so helpful.
ReplyDeleteI have a question for Miss Bouffant. If you were the stylist in caption #4, what style would you suggest to the Mother of the sissy in your chair?
DeleteHmm? The Sissy appears to be young, possibly in "her" early 20's. I believe the mother might be correct. The Sissy has grown out her hair to look "Cool" I would imagine? What better way for Mummy to exhibit her control and dominance in the situation than to decree a short styling, such as a severe undercut with a tight perm on top. I can imagine how vulnerable the prim Sissy just might feel when the mother's boss's Alpha Male son puts his Beefy arm around her as they walk into the "Drag" bar on their very 1st of many date-night's out.
DeleteI agree with caption #2, however one purse would never be enough. A sissy might start her collection with a wristlet, move up to a clutch, then a hobo. Eventually she will begin to carry a satchel which will hold a make-up bag, a spare pair of pantyhose, a hairbrush, panty shields , hand lotion and condoms. A sissy would never leave the house without her purse.
ReplyDeleteSome sissies spend countless hours on their knees attempting to convince their Husbands to build them a shoe and purse closet to display their collection.
Donna
Pretty clothes, purses, shoes and salon pampering's are all well worth getting on my knees for.
DeleteYou are a smart sissy. Do you have a dream purse that your boyfriend/ husband will eventually have Santa put under the tree for you?
DeleteDonna
Donna, do not forget breath mints, and possibly a travel sized bottle of mouthwash? We would not want traces of anything on your breath
DeleteMy favorite in this pile is the "Sissy Problems" one
ReplyDeleteYou have a way
ReplyDelete