How I spent my summer vacation – Episode 4

It has been quite a while since I have related another of my summer experiences with Mistress Rosemarie. I was supposed to do this on a regular basis, but forgot and to be honest put it off since my summer vacation was mostly humiliating with many embarrassing activities, trips and things with her. Well the year is almost over and as all things do it has caught up with me big time. This past summer often found me in hot water, but none more so then when I tend to embarrass Mistress Rosemarie in front of one of her friends.

The specific day was a nice warm day in August and we were suppose to go to the beach with one of her friends from work. This was always fun and mostly stress free for me since Mistress Rosemarie was seldom inclined to embarrass me in public by having me do girlish things. It was Saturday and when we went to pick up her girlfriend she explained that she had her period, did not feel good and really did not want to go to a sandy beach. I had been looking forward to this and I lost it. I cried and before I thought, I said I didn’t care if she had her period, she could stay home and we should go without her. No sooner were the words out of my mouth and the look on Mistress Rosemarie’s face told me I had crossed the line. I knew it was insensitive and I knew I would regret it.

Mistress Rosemarie left the room with her friend and when they came back smiling they told me it was about time that I had my first feminine period. I blushed a deep red, but knew better then to say a word. Well out came the feminine sanitary products and their fun began and my misery started. Her friend seemed to feel better that she had a girlie sissy to commiserate with. I was very much embarrassed by this day that I had hoped never to have to relay it for all to hear.

I somehow never learn my lessons though. Last week I made the same awful insensitive mistake again with another one of her friends because it interfered with us going out to a party. She was totally livid and then she remembered my unlearned lesson from this past summer.

Well, this has now become – How I spent my summer vacation – 4 and also how I spent my Christmas vacation – 1.

This past Tuesday Night I came home to find Mistress Rosemarie with both of her girlfriends that I had embarrassed by being insensitive about their periods. They reminded me about how I had said to all of them that I did not see what the big deal was about a little stomach ache and having to wear a rag between there legs. Well, Mistress Rosemarie then smiled and said that it was about time that I realized what a big deal it was.

I was led into the bathroom and spread out on the counter was my impending lesson.


I was to have my first feminine period and I would certainly learn what the big deal was after 24 hours. I groaned, but there was no way out of this now.

They told me my period would start at 11:00 PM this evening and end tomorrow night at midnight.

The girls had come up with a way for me to experience a girl’s period cramps. Enemas would certainly do the trick they said and I knew this was not going to be pleasant. They gave me a sheer peignoir robe so nothing would be hidden. I was to be given a two quart enema at 11 and if the cramps were so bad I could not stand them, then I would be allowed to got to the toilet, but the enema fluid would be replaced with an equal amount. I would also have clothespins attached to my nipples so they would become sore just like a women with her period. This would go on till midnight.


I was bent over and the feminine enema nozzle was shoved roughly into my sissy vagina and I cried as they laughed at my discomfit. Then a pin was snapped on each nipple as I cried again as they giggled.

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Down on the bed and the enema fluid was let loose. As it always does, the cold water rushing up my rectum into my stomach caused instant cramping and much discomfit. I was bloated in a matter of minutes and lay as still as I could on my bed. They laughed and as they were leaving me to my discomfit told me to call if I needed to go to the toilet. In ten minutes the cramps were horrible and in twenty I was crying and squirming on the bed, but the cramps would not subside. After 25 minutes I cried out for mercy and they led me to the toilet to relieve myself. I was given only one minute to relieve myself and was then led back to the bed.

Mistress Rosemarie then said she did not know how much I had released, so therefore I would have to be given a full 2 quart enema again. I cried that she knew I always retained at least have after a minute, but she said too bad. She opened the clamp and the flood of enema fluid slammed through my system with even greater cramping. I was crying almost immediately and within 15 minutes I was begging to go to the Toilet again.

I was filled up again twice more in the hour and when I was finally allowed to sit for 5 minutes on the toilet at midnight, I know I still had at least two quarts left in me.

Finally I was led back to the counter and a sanitary Napkin and tampon were waiting for me. On the Sanitary Napkin was splattered red jam to simulate my period.


I was forced to put the soiled sanitary napkin in my panties and then one of the girls inserted a tampon up my sissy vagina. Oh how it hurt at first. In fact, I never did get use to having a tampon up my sissy vagina. I pulled up my panties and put on my negligee to sleep in. I was really hurting with the cramps that continued.

Every hour I was also awoken and given a large glass of water to drink which bloated me further and my stomach ached even more. This continued for 24 hours.

I was then told that for the next 24 hours I would have to change my pad and tampon everytime I went to the Ladies Room, but at a minimum at least every two hours.

It was 2:00 AM when I was awoken and led to the Ladies for my first sanitary period changing. First my soiled pad and tampon were removed and new put in its place.

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This happened twice more during the night and it was so disgusting and I could not sleep. They told me that a girl always has trouble sleeping with her period, so why shouldn’t I.

Finally it was morning and I was dressed for work. Another new pad and tampon, a very small bra so I would feel my breasts all day and be totally uncomfortable were put on and in me. They also gave me hand fulls of sanitary napkins and tampons to carry with me. I put them in my backpack, but I was told I had to carry a pad and tampon in my pocket just in case. I was so self conscious that some one would notice.


Finally my day at work was done and that included going to the restroom and changing my pad and tampon every two hours. I returned home with my soiled feminine products in baggies to show that I had done it. It was really disgusting.

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After all that, I was finally allowed to change into a comfortable soft nightie to relax if I could the rest of the night. I curled up on the coach because my stomach still ached and watched a movie.


At last it was midnight and my period was over, but first I was led into the bathroom to see some of the tampons and sanitary napkins I had used. What a pile and that was only about a third of what I used. She said she would leave them there for a day or two to remind me of period.


Mistress Rosemarie asked me if I thought a feminine period was still not so big a deal. I cried and said I was sorry and that I would never make fun of a girl with her period again.

Then, as always, she dropped one last bomb. Mistress Rosemarie said that once a girl gets her period she has it for the next 40 years. Therefore, since I now had my first period, it was only fair that it continued. So – 28 days from now – the 28th of every month, I was going to get a visit from my menstrual friend and I would have my period for three days each month and would have to use the necessary feminine products with the middle day being the heaviest flow requiring both a pad and tampon.

I was then sent to bed with tears in my eyes and definitely not looking forward to my monthly “friend” visiting.

A big sissy like me should learn to keep her mouth shut.


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Dear sissy billy,

Thank you for sharing your adventure here. I also wish everyone a happy new year.

Hello pieclown,

Most of my adventures are meant to be humiliating and this certainly was, both the experience and the sharing.

I also wish you a Happy New Year and hope that yours and every one’s New Year is better and healthier than this last year.

Hi Sissy Billy,

But you should be proud of what you went through, and well done for sharing it. I think it is something all us girls should think about.

I hope you had a wonderful Christmas and New Year,


Trish xx

Hello slut_tricia,

It was not fun having my period and I sat at work thinking about it and feeling embarassed each time a girl walked by. As I sat in a few meetings with other girls in attendance, I wondered if any of them was having their period. I do have a new found respect for a girl and her period as Mistress Rosemarie intended. I probably only got a small idea of what a girl experiences each month.

Mistress Rosemarie was serious about me having my period each month now as she reminded me that it would come again before I realized at the end of month and I better go to the store soon and make sure that I have enough feminine sanitary products and that I was prepared.

I did promise her that I would make a comment here when my period came again, so my period will continue to be shared among my sissy friends.

I hope all of you had excellent Holidays and are energized for the upcoming year.

sissy billy

sissy billy,

You have been very quite all month, but you should not be embarrassed by your period. To all who don’t know what time it is, it is the end of the month and sissy billy is having her monthly period. It started on Friday and I am thinking it will last three days this month.

I expect you to comment sissy billy and tell everyone how you did this month with your feminine menstrual cycle.

I have been instructed by Mistress in very strong terms to tell everyone each month about my feminine period. My period this month is to last 3 days per Mistress.

My period started on Friday with three enema induced cramping sessions and as before was very unpleasant. I wore a sanitary napkin for the rest of the day. The cramps continued all day as I was required to drink water constantly.

On Saturday I kept a pad in my panties, added a tampon, wore it constantly, changing it often and each time I had to go to the bathroom, which was often with all the water that I was forced to drink.

Sunday, the last day of my period I was allowed to stop the tampon, but had to keep the pad in my panties. This did not seem so bad though because I was also completing my Happy New Year 2011 – Again assignment/punishment.

Monday, my period was ended, but I know another one will come again in 28 days and Mistress tells me it will get worse as I go through my sissy girl “puberty”.

Hello Mistress Katzenburg and all of you other sissies:

sissy billy has been very quiet and probably because her time of month was here. As quiet as she is I could not imagine letting her slip under the radar during such an important time in her sissy training.

It is sissy billy’s monthly feminine period and there is no avoiding it. As she develops through her girlie puberty her menstrual period will last four days this month.

Thursday Night – A two quart enema every hour till midnight to induce her feminine period cramps.

Friday was to be a light day and she only had to wear a Kotex day pad. Of course she is instructed to drink water every hour to help with her bloating and change it every two hours.

Saturday & Sunday she is to have her full flow period needing a Kotex maxi or overnight pad and a tampon in her sissy vagina. Of course I concocted a rather bloody looking mess to fill her feminine napkin.

Monday will be another light day for her to wind down.

Do not worry sissies – she has been told to add a comment to this Post on Monday night giving you all the very unpleasant feminine period details.

Mistress Katzenburg – I instructed her to take pictures for your personal inspection. I have seen her taking pictures, but I don’t think she has uploaded any for her Mistress’s Inspection. I will remind her.

I just love it when my sissy experiences the feminine things that she never wanted to.

Mistress Rosemarie

A sissy’s period should not be for public exposure, but Mistress Rosemarie does not seem to think so. One should be able to keep her private life and experiences a secret if she wishes.

It was my time of the month and it was worst then last month and lasted 4 days this month.

Thursday Night – Mistress made sure this time that I experienced full feminine cramping like she did. With an enema every hour for six hours my tummy hurt very much and did not stop hurting until Monday morning. I was also forced to constantly drink water for that bloated feeling and made to take many doses of Correctol (some kind of women’s laxative).

Friday was not so bad except my cramps, but I had become accustomed to wearing a pad.

Saturday was a different story. I was given a messy red sticky gooey pad to wear as well as a Tampon in my sissy vagina. My stomach ached, but since Mistress Rosemarie was traveling on Valentines Day, she decided we would celebrate Valentines Day on Saturday Night and I would be dressing very formal and pretty for her. This meant a formal Prom type gown with heels and accessories and of course makeup. I did dress pretty for her, but feeling terrible from my period all I wanted was to go to bed.

Sunday was better as I was allowed to lay around the house in my comfy Nightie.

Monday – Finally all I had to wear was a clean pad and it was over on Monday Night.

Feminine Periods are not fun and Mistress Rosemarie just told me that from now on I could expect a full 5 or 6 day period each Month. I am not a happy sissy camper.

Mistress Katzenburg, I have uploaded as is required pictures of my period for your inspection to the sissy dropbox.

Glad my period has ended, sissy billy

    Hello sissy billy,

    I wish to warn you that you line about keeping you sissy life private. Was it not you waning to become a better sissy and ask to join here? I am not saying make it know to everyone, but sharing here allows your sister sissies to say “Ah poor baby”.

    I wish you well

Hello pieclown

You are correct. I joined wanting to become a better sissy and knowing that I must accept my punishments for Cross-Dressing. That was just a bit of feeling sorry for myself. Sometimes sharing completely is a bit humiliating. A bit of criticism from you is always accepted. Thank you for correcting me.

sissy billy

My humiliation does make my Mistress laugh as I am sure it also makes Mistress Katzenburg laugh.

    Hello sissy billy, I have to admit I have smiled at some of your adventures here. Some time it is because I did not have to do it.
    You have a good one and stay healthy, I think I am catching the sickness that has been going around.

    pie pie 4 now

Sissy Billy, Stop complaining, You got what you needed, Sissy Period Training, Your Mistress knows what’s best for you. Think about the girls that have there Period for 7 to 10 days or a Prostute on her period for 7 – 10 days, and having to service her customers day & nite, putting a smile on and giving blow jobs every 15 mins. Your a lucky girl it could be a lot harder. Every Sissy should have there Period every 28 days, and have to go to the store to buy Maxi-Pads & Tampon and when asked by the female store clerk if that need help, have to say, Yes, I need some Maxi-Pads and Tampons for my Period. It all part of being a Girl.

So Sissy Pad Billy, did you learn anything, are you enjoying having your period ???
Kotex Knows….

Please don’t make fun of me Cody, it is humiliating and very unpleasant. You should try having you girlie sissy period sometime.

My sissy period for 4 days was bad enough and very unpleasant. I can’t imagine a girl having a really bad period with cramping for 7 days or more, but Mistress Rosemarie promises me that this last sissy period was not as terrible as I made it seem and I should expect my sissy periods to get longer and more disgusting like a real girl’s period. I had PMS after just a four day period.

I do have to go to the store and buy my own Kotex Pads and Tampons. She also makes me go to the store and buy more during my period while I am wearing a gooey icky sticky disgusting Sanitary Napkin and tampon. I have not had to answer any questions because the Sales Ladies don’t say anything, but they do look at me and I am humiliated when I have to buy them. Most of the time I try to use the scan lines where there are no Sales Ladies and I can pretty well hide what I am buying, but this last time Mistress Rosemarie stopped at a CVS and made me go in and buy tampons and Kotex and I had to stand in line with a other women and buy them from a Girl at the register. Very embarrassing.

Not looking forward to the end of the month and my monthly feminine cycle, sissy billy

I hope the girls allowed you to take a nice long soak in a scented warm bubblebath. I always feel better after that.

Hello sweetsuds,

Very nice to meet you.

Yes, Mistress Rosemarie did allow me to take a pleasant hot bubble bath, but not after giving me a final enema to cleanse me.

After my bath she always has to add a humiliation though. She perfumed me and then we went shopping at the supermarket. I tried to stay close to her so as we walked by other women they would not notice that the pretty perfume smell was from me.


sissy billy

sissy billy’s Period Diary – 3-27-11
Sunday – 3-27-11
8:00 AM – Put light Day Pad in my Panties. 12:00 Noon – Change my light day Pad for another light day Pad. I am getting use to the pad again, but it is embarrassing whenever I feel it and I think of my period. 4:00 PM – I now have to drink a 12oz glass of water every 15 minutes for three hours. After three hours I am bursting, but what is worst is that I now have a lot of cramps. My period has come. 8:00 PM – I put on a overnight Sanitary Napkin and try to go to bed. My cramps are worst and now the rule is the remainder of my period every time I go pee, I have to drink a 12 0z glass of water.
Monday – 3.28-11
6:00 AM – I did not sleep well and I have lots of cramps. I put on my Pad doused in blood, put a tampon in my sissy vagina and pull up my panties and go to work. 10:00 AM – I have excessive cramping now since I am bloated and the tampon is stopping me from having a bowel movement. Finally I change my Napkin and Tampon and the cramps lesson. 4:00 PM – I have to leave work early because of my cramps. When I get home though, Mistress Rosemarie says she would like a nice dinner and I should get dressed. I started to whine, but stop quickly as she said she was going for soap. 8:00 – I suffered through Dinner almost crying, but finally I was sent to change and put on a nightie, of course with a Napkin and Tampon Change.
Tuesday – 3-29-11
6:00 AM – I did not sleep at all last night and I really was cranky. I was told that the worst was over though and I did not have to keep drinking water. I changed my Sanitary Napkin twice during the day, but at least the cramps were subsiding. 9:00 PM – I was allowed to go to bed early and I did. Wednesday – 3-30-11 – My period was ending thank god and I was back to a light day pad.
This was my worst period ever and I it is only 28 days to my next period. This is terrible being a sissy girl with a period.
Sissy billy

By reading this I have realized how big of a deal a proof can be. This assignment definitly sounds like no fun at all. I also will not be giving any girls any lip about their periods from this point on.

My mistress makes me have a period each month. I have to take a laxative to have cramps, and bloating each month. I have to wear a bra, and panties pads and tampons each month to bed. I have to wear a pad and diaper each night during this time, so I do not make a mess of the bed. Every morning, I have to get up super wet from the night. That means I have to pee in the pad.

love what the girls did i think mistress should make him wear her used one when she changes hers and make him use femfresh perfume

    It had always been my fantasy and desire to be feminine and “Girlie”. Of course I never wished to be a Sissy full time, just part-time when I wished. As my Sissy Cross-Dressing Punishments continued, Mistress told me I needed to experience both the dress-up, humiliation and also the difficult times that a female experienced I was not so confident in my wishes. Mistress then told me that I must experience having a “Feminine Period”.
    The cramping from the pills and many enemas was horrific. Mistress just laughed and told me my cramping was not even close to feminine cramping. Then the constant use of Feminine “Pads” and Tampons was uncomfortable and so humiliating.
    Your suggestion of using the dirty Pads is so “ICKY”. I am glad she did not think of that at the time.
    Ms Jilly – If you are suggesting this, maybe you should also wish for this very feminine treatment. But, as I have learned, be careful what you wish for.

Hello Mistress Rosemarie,it’s nice to know that the bar of soap is still being used for backtalk and potty language the more the lather the better in dealing with this problem just ask sissy Stephanie who receives the soap on a monthly basis.

                        Mistress Tyra

My Mistress Corie simply places her used pads in my panties when she changes them covering my clitty up and I sit on her used pad all day, until it’s time for a change, either hers or mine. I’ve never inserted a tampon in my pussy…I keep a plug in and love having it in when in public. I just rock back and forth on it wherever I am. BTW, this is my first post. I’m SissyScarlett and have so many questions for you gurls.

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