Aunt Flo is in Town!
pennydickless | 06.21.2019 | Reports - Womens Studies

What a thrill it was for penny to receive notice that she would be truly becoming a female, and be initiated into mother nature’s gift. Immediately after receiving the message that Aunt Flo was arriving, sissy excitedly prepared a list and went to the local drug store. By way of backdrop, when penny was with her natural Superiors (i.e., Women), she was thrilled to be able to perform cunnilingus on her ex-Wife (who, perhaps not surprisingly, left her for a Lesbian, although that was more due to the size of penny’s clitty than the quality of the cunnilingus) when She was flying her colors – penny loved the opportunity to lick the discharge and all of Her special parts, and have her face covered in the crusty, tasty, Wonderful gift . To this sissy, there is nothing more appropriate than to orally worship Women when they are having moon time – penny was also fortunate enough to engage in the same practice with subsequent Womenfriends. Yes, this sissy has earned her red wings, several times.

So, when sissy received the message from Aunt Flo, as noted above, she first went online, as instructed, to the website. She filled out the (product recommendation) quiz on the website, and also registered the beginning of her period (she assumes that, in addition to receiving notices from the House regarding her periods, she will also receive a notice from the makers of these wonderful products). Penny then went to the drug store to prepare for her impending discomfort. Although she did not have enough courage to fully cross-dress, she did put gloss on her lips and wore yoga pants – when the next period arrives in 28 days, she will definitely do better. She somewhat shyly went to the aisle with feminine products, and, as per the instructions, purchased a number of products, including maxi-overnight pads, and super tampons (although penny has not been penetrated by a real penis, at least not yet, she has played with her sissy hole, so she should be able to take super tampons – this evening, as nature takes its course, she will see if this is possible). This sissy also purchased some panty liners for the rest of the week, as the maxi-overnight pads might be too visible when she goes to work – she then proceeded to the area of the store which had laxatives and midol – she purchased the female laxative correctol as well as midol of course. When penny checked out, the female clerk looked at her rather curiously, which made sissy’s little clitty become erect. To further the humiliation, penny took one of the panty liners out, and asked where the restroom was (and, of course, after entering the restroom, proceeded to carefully place one in her white cotton panties).

This sissy is now home, and the correctol seems to be taking its effect – penny is experiencing cramps in her stomach and bowel area – how wonderful. She will endure these, and tonight, will take one of the overnight pads, smear it with molasses and ketchup (to simulate the wonderful crimson color of nature’s Gift, of course) and wear it all evening. In addition, she will insert a super-maxi (tampax) tampon – hopefully she will be able to make it through the evening, until more of Aunt Flo arrives in even greater glory tomorrow. Will penny be able to endure these 5 days? Actually, she is looking forward to it, and even moreso looking forward to next month, when, as we have been told, the period will be even more intense.

Penny (not intended to capitalize – it’s that damn spell check, most certainly a male invention) is eternally grateful to the House of Sissify Staff, and, of course, especially to Aunt Flo, for allowing her to join the MUCH BETTER half of the world – because she started all this too late, penny will value her shark week even more as she moves forward.

humbly and submissively, penny


  1. wow, this sissy just re-joined the house and forgot all about aunt flo. to make matters worse she gets joined for a year and gets her assignments from the staff, so she has no control over wether or not she gets the aunt flo humiliation assignment. good luck with your period sister.

Something to share sweetie?