Day 1: sissy read the assignment thoroughly to ensure s.he understand the intent. s.he then went to the store to purchase the needed feminine hygiene and other products. To prepare for the shopping trip, sissy put on female jeans, a small bra and panties, a yoga top under h.er women’s fleece jacket. s.he applied a light coat of mascara, tinted lip conditioner, a tiny bit of crème eye shadow, perfume and some light face powder.

As sissy walked into the store, observing all the real Women there, s.he had two overwhelming thoughts. One, excitement that sissy was about to join the menstruation club (at least as closely as s.he can). Two, sissy wondered how many of these Women were currently dealing with Aunt Flo as well. Both thoughts made sissy smile widely as s.he made slight eye contact with these inspiring Women.

As sissy approached the feminine hygiene product isle, s.he had to overcome an initial desire to just grab the first package of pads and tampons within reach and move on before someone noticed. sissy took a deep breath and began to carefully read the various product descriptions on the packages of both the pads and tampons to make sure s.he got the correct ones. With large packages of pads and tampons clearly visible in h.er hand basket, sissy proudly moved on to the medicine isle to find the midol and icyhot. With the medicine added to the basket, s.he moved on to find something to use as nipple clamps. This store didn’t have any spring loaded clothes pins, so sissy thought of substituting the type of spring clips used to seal chips or snack bags. With all the necessary items in the basket, sissy proceeded to checkout and return home.

As After returning home, sissy chose the “lite” flow size tampon, applied a bit of lube to h.er sissy cunt and and inserted it, following the instructions included in the box. Before pulling up he.r panties, sissy applied one of the maxi pads inside he.r panties making sure it was positioned properly. Next, s.he took two of the midol tablets and drank two full glasses of water. Finally, sissy take applied a bit of the icyhot to he.r nipples to initiate nipple sensitivity and put on the nipple clamps for 2 minutes.

Before bed, sissy removed the tampon and replaced the maxipad for overnight, and drank 3 glasses of water.

What sissy learned today: 1. Fuller cut panties with a wide gusset are better for holding the large maxipads in place. 2. Wow, sissy’s nipples are really sensitive after the icyhot and clamps! 3. The tampon and maxipad constantly remind sissy of aunt flo’s visit with every move.

Day 2: When sissy awoke, s.he was very aware of the extra bulk in he.r panties from the maxi pad. After taking care of morning potty needs, sissy selected a ‘super’ size tampon as day 2 should have a heavier flow. s.he generously lubed he.r sissy cunt and inserted the tampon, double checking that the string was still in the right place. After showering and shaving legs, and applying body lotion, sissy put some extra lotion in he.r crotch area to simulate the moist, sticky feeling natural Women must experience at some point. Before putting on panties, sissy applied a small amount of strawberry jelly to the center of a new maxi pad and slid it all in place. Positioning panties properly with the extra bulk of a large maxi pad was a little different than normal. Sissy then applied a little icyhot and the clamps to he.r nipples while finishing getting ready. After finishing getting dressed for the day, sissy was somewhat worried that the bulk of the maxi pad might be seen through he.r pants, especially if s.he bent over.

Before a cup of coffee, sissy drank two more glasses of water and took he.r morning midol. As work was only half a day, sissy only packed one extra tampon and pad in he.r bag just in case. Off to work!

At about 9:30 am, the cramps started! Wow, it was really uncomfortable and difficult to concentrate. As sissy was in a meeting, s.he was unable to leave for the sissy lounge for about :30 minutes. Sissy had not taken any medicine at this point to induce the cramps, they just came out of nowhere. Finally sissy was able to attend to bathroom needs, when all finished, s.he was glad s.he brought the extra tampon and pad. More water. The rest of the afternoon was rather uneventful. The cramps subsided, but sissy had to ‘go’ a lot more from all the water and really did feel bloated. After dinner and getting ready for bed, sissy changed out the tampon and pad and applied more lube and took two more midol with 2 glasses of water and wore the nipple clamps for 10 minutes.

What sissy learned today: 1. There was always a constant voice in sissy’s head wondering if others could tell s.he was cramping or could see he.r pad through he.r pants. 2. Cramps are uncomfortable. 3. Always have extra feminine hygiene products in your bag, you never know when you’ll need them. 4. Nipples are more sensitive.

Day 3: sissy had the same daily routine as day 2, but the fear of others noticing the extra bulk in he.r panties was less.

What sissy learned on day 3: 1. The bathroom waste basket needs to be emptied more often. 2. Chocolate does make things better!

Day 4: Pretty much the same routine as day 2 & 3. What sissy learned today: 1. s.he missed he.r special day and must wait another week. Wasn’t really feeling very sexy with all this going on anyways. 2. Extra lube makes the tampons much easier to insert. 3. Happy this only happens once a month.

Day 5, last day!: After waking up and taking care of bathroom business, sissy was happy to go back down to the normal size tampons and small panty liner from the heavier maxi pads. Mentally, sissy was really really beginning to empathize and happy to have some small awareness of what real Women deal with every month from puberty to menopause.
After getting home from work, s.he removed the last tampon and pad for this month and took a nice, hot, long shower.

What sissy learned on day 5: 1. sissy actually felt a little less clean and fresh than normal, taking the hot shower and cleansing well with a douche made he.r feel fresh and ‘right’ again. 2. sissy’s sex drive was returning, but alas, s.he will need to wait a few more days before he.r next approved special day. 3. sissy feels much more feminine and satisfied inside for having starting this special ‘initiation’ into womanhood, or rather sissyhood!