The Assignment: Wearing women's clothing (see below)go to a cosmetics counter at a department store and get advice about foundation and lippy.

i'm behind on my blogs, but i had the most wonderful shopping excursion, so i'm skipping ahead a bit... The entry that follows was originally intended as an email to Mistress, but it got kind of long, so i'll use it, slightly revised, for my blog instead.

On Monday, i was supposed to go shopping with my friend here in Ottawa, but everything went wrong (pout). At the last minute, he told me he had too much work, and couldn't make it, but i convinced him we could just start a bit later. i got myself all ready: tight low-rise jeans with the waist of my panties peeking out, stay-up stockings under my jeans [i know You wanted me to wear a garter belt and stockings, but i don't have any appropriate stockings to go with a garter belt right now... sorry...], white blouse with my mauve bra showing through subtly [and matching the ruffles on the waist of my panties quite nicely, i thought], and of course my 'sissy' necklace and my lippy and clear mascara.

i was nervous as hell...

He came and picked me up just before 7 in the evening (Of course, my neighbours who are never around had to be out in the driveway!); i was really shy meeting him, but we had a nice chat during our drive to the mall. it was pretty exciting for me, dressed as a girl in a car with a man, but i was too nervous about the mall to think about anything naughty... at least not much (giggle).

When we got to the mall, i was really glad he was with me. i was so nervous just getting out of the car and crossing the parking lot. Not that there was anyone in the parking lot, because, as we were to discover moments later, the mall had closed for the night at 6pm! we chose the only mall in a large city in all of North America that closes before 9pm... Mistress, as nervous and shy as i was about going dressed to the mall, i was terribly disappointed... My friend couldn't go anywhere else, since he would run into people he knew at any other mall, so he brought me home and my adventure ended. As i drove away i realized that i'd forgotten to ask him if he'd brought his camera... at least i could have gotten a piccie of myself out and about for You... oops...

So Monday night shopping fell through, and i still had my assignment to complete. But how? i don't want to disappoint You, Mistress, and i really, really want to go shopping and get makeup advice, but i have no one to go with, and i'm still way too shy and scared to go on my own...

What is a sissy to do?

Tuesday, i took everything i would need for the shopping expedition to work, and after work made the same preparations as i did when i went shopping before (bra and blouse under boi shirt for the bus trip across town, etc). Even as the bus started across town, i was composing in my head the email of apology and contrition in which i admitted to You that i had failed utterly to go to the mall in girl's clothing; i just couldn't imagine any way i could get past my self-consciousness and irrational fears. But i had to try...

So to start, i went back to the thrift store where i went shopping a couple of weeks ago, once again doing so in my blouse and bra, and this time with my 'sissy' necklace as well. i tried on a couple more pairs of jeans, and found a nice pair... girl's jeans, but a little less overtly so than my previous purchases, and a little easier to wear in a mall for the first time, maybe... (i also picked up a sweater... no more excuses about the cold for me! [giggle])

i crossed the road to the mall, and changed into my new jeans and nylon ankle socks in a men's room stall. And then i walked out into the mall... But Mistress, i wasn't quite as brave as i might have been... it was raining that day, and i did keep my long overcoat on. But the coat was open, and i was wearing girl's clothes for anyone to see.

For my first stop at the mall, i went to a shoe store... they had a buy one pair, get one pair 1/2 price deal on. (i wish i had painted my toenails, i could have completed that earlier assignment) i bought a couple of pairs that should help me get used to walking outside in ladies' shoes... (giggle) But i wasn't brave enough to wear them through the mall...

Next i went to a department store. i browsed the lingerie department, and then went to the cosmetics department. i had no idea which counter i should go to, so i went to MAC. i was very shy at first, explaining what i wanted, but the girl was so very nice, she really put me at my ease. When i asked her about tones and colours, and she told me the only way she could tell was to try them on me, and if that was ok... i put aside my reservations and let her work her magic. There i sat, getting my makeup done, lots of people walking by. My 'sissy' necklace was partly covered by my blouse, but there is no way the girl doing my makeup didn't see it (giggle). She gave me lots of advice about skin preparation, and makeup application, and even tips about how i could use the same subtle, natural, everyday makeup to create more 'dramatic' effects. Mistress, i know i was only supposed to get my foundation and lippy, but i went a little overboard; i bought everything i needed, though i took the nice girl's advice against buying their brushes, as they were fiendishly expensive.

Of course, it was only after my makeup was done that i realized i had no way to remove it... and i really didn't want to (giggle). So i went back out into the mall, showing the world my new girlie face. (i only wish my hair hadn't looked so awful and unfeminine.) If You had asked me an hour before if i could do that? No way... i must have passed a hundred people or more, and i can count on the fingers of one hand the number of people who even gave me a second glance.

i felt like i could go anywhere, do anything. Always too shy and scared before, i walked into La Senza as if i went there everyday and treated myself to some new panties. And then i walked through the mall with one of their dainty little shopping bags... i must have looked like such a sissy (giggle).

i had to wash off the makeup before going home (pout), but i wore my girl's clothes on the bus, (though still with the overcoat... )

i spent the rest of the evening giddy with excitement over what i'd done, and what it might mean for what i can do in the future. i must have worn the biggest smile most of the next day at work (giggle); even the brutal grind of my job could barely touch me. Even now, a couple of days later, i smile everytime i think about it... and i'm almost always thinking about it.

Thank You, Mistress. i don't remember the last time i was this happy.

And now i have only one thought on my mind: i have to do something about my hair! (giggle)

Next: i don't know yet, but i'm dying to find out!

The Assignment: Originally the assignment was to wear a bright red bra under a white shirt while shopping for a bra. When Mistress saw a couple of my pretty blouses, She decided i should wear one of them instead of the white shirt...

Status: Complete

OMG i was so scared when Mistress assigned me this task... Openly wearing girls' clothes in public? Just like that? Scary, but with just the right hint of that delicious humiliation that a sissy craves...
i knew if i didn't do it soon, i'd never have the nerve. So the very next day, i made my preparations, taking everything i would need with me in the morning. After work, around 2pm on Tuesday, i went to a nearby public restroom, and got ready to go. i changed into the bra and blouse (see my piccies, the one called assignment #3 to see what i was wearing...), putting my boi shirt back on over the blouse for my journey across town [of course, i was also in panties... Mistress no longer even allows me to own men's underwear]. i applied the clear lip gloss and clear mascara that Mistress has me wear at all times (except at work... thank You, Mistress)and checked the clear polish on my fingernails before i left to catch the bus.

On the bus, on the way across town, i listened to my feminization hypnosis mp3's... i don't really believe in hypnosis, but they tell me things i want to hear, and really helped to put me in the mood to be a good obedient sissy. When i started the trip across town, i wasn't sure i could go through with the assignment, but by the time the bus reached my destination, it almost felt inevitable that i would...

From the bus stop to the store, a walk of about 5 minutes, i dared to open my boi shirt and allow my pretty blouse to show, but i still couldn't take off the overshirt to expose the puffy shoulders of the blouse... i wasn't THAT brave...

The store i had chosen is a large thrift shop where i had shopped for girls' clothing before. In fact, the blouse i was wearing came from that very store. As i neared the store, i was plagued with doubts... Could i really do this? Would i be too embarrassed, feel too self-conscious and ridiculous to proceed? i walked through the doors... the moment of truth... i knew if i didn't take off my boi shirt right away there was no way i would be able to do it... And i remembered Mistress's advice when i expressd my reticence and fretfulness about the assignment; She said to stop thinking about it, and just do it.

So i just did it.

i did it. There i was, in the middle of the store wearing a pretty red blouse and bra for everyone to see... And everyone just went on about their business. Of course, i didn't notice that at first... my mind was racing and i was SO sure the sky was going to fall in. i spent the next 5 minutes staring at skirts, and not seeing anything... Eventually i regained control of my faculties, and set about my business... shopping! i was supposed to be shopping for a bra, but of course since i was in the store anyway i thought i might as well look at some other clothes that i might need. Over the next half-hour, i found a bra, a blouse, a belt, two pairs of women's low-rise jeans, a cute little miniskirt, and a ridiculously frou-frou pink party/prom dress. i was still not entirely comfortable and secure, dressed as i was, but very few people seemed to pay me any attention. i think some teenagers were laughing at me. Still, i was shy and furtive, and avoided crowded aisles.
i had found the items i wanted, or needed. When shopping for girl's clothing, usually at this point i would head straight for the cashier, too shy to even consider trying things on in the store and admitting to everyone present that i am buying these things for myself (blush- as if i'm fooling anyone). But that day, wearing that blouse and bra... i'd already made that admission and i had nothing else to be shy about. i walked up to the girl in charge of the changing rooms and asked which i could use; she wasn't paying that much attention to me, but there is no way she could have missed the ridiculously frou-frou pink party/prom dress that i took in to try on (giggle). [Keep an eye out for piccies of all my purchases that day, incuding the ridiculously frou-frou pink party/prom dress.]
The most embarrassing part of my shopping expedition was still to come. When i went to the cash to make my purchases there was only one cashier open, but only one woman in front of me in line. Unfortunately, she was determined to pay for all her purchases that day with a pile of coins that she spread out across the entire countertop. It took the cashier and the customer FOREVER to count those coins. And i just had to stand there in my bra and blouse, girlie items in hand, including (very obvious to anyone who might happen to glance over) the ridiculously frou-frou pink party/prom dress. Unlike the rest of the store where i was relatively hidden down the aisles, i was completely out in the open waiting at that cash. i think i turned purple with embarrassment before i finally got to buy my new clothes. The girl at the cash made no comment about the ridiculously frou-frou pink party/prom dress... for which i am very grateful... and i went on my way, throwing my boi shirt over my blouse as i crossed the parking lot.
i had spent an hour in the store, wearing a blouse and bra in public. i had a huge bag of new clothes... and it only cost me abot $60!

Things i learned: Most people don't care what i wear or what i do; they have their own lives to attend to. i probably knew that anyway, but it is good to have evidence of it. Also, it's a lot easier to shop for girlie things when i'm not trying to hide the fact that i'm a sissy. i have to be honest, upfront, and forward about who i am, and get any potential embarassment out of the way so i can go on about the busines of becoming the girl i want to be. (giggle) i feel very clever...

Next: Out for a late night stroll...

The Assignment: With painted nails under sheer nylons, go to two shoe stores and get assistance trying on shoes, men's or women's.

Status: Pending

The second task is very difficult for me, and not as much for the obvious reason. i mean, sure i'll be embarrassed to expose my sissy painted nails and stockinged feet... but that's not my main concern. i worry more about asking for help ...i hate to ask for help if i really don't intend to buy anything, as would be the case were i to shop for men's shoes. And i'm often very shy about asking for help with my girlie shopping.. i know that's something i have to get past... but i'm not there yet. Mistress has very kindly allowed me to defer this assignment- thank You, Mistress- perhaps until such time as i need new shoes?

Next: Things heat up when genni finds herself with another shopping assignment...

The Assignment: Go into a store to purchase ONLY a cucumber, a packet of condoms, and a tube of lube, and be sure to make the purchase from a female cashier.

(giggle... i didn't get this one at first... i tried to explain to Mistress that i already had condoms and lube... i can only imagine Her rolling Her eyes at Her silly little sissy's incomprehension as She explained that that wasn't the point...)

Status: Completed

This first task was relatively easy. The suggestive nature of the purchases was a little embarrassing, but there was no way i was going to let that stop me from completing my very first assignment for Mistress. Actually, my only hesitation resulted from my unease with 'involving' the cashier in the assignment without her consent. After all, the potential embarrassment of the purchase only works if the cashier infers my intention to use all three articles together... (giggle) Probably i'm too sensitive, but i worried that it might not be fair to put her in that position.
But my understanding is not required, only obedience.

The Proof:

Next: Off to the shoe store... or not (blush)

Hi everyone. my name is genni (obviously, i guess (giggle)). i'm 39 years old, and i've been dressing (mostly privately and secretly) as a girl on and off since i was about 12. i admitted to myself a long time ago that i am a sissy, i've just had a very hard time showing it to the world. The last few years especially i have struggled to move forward with my feminization, wanting to acheive passability and go out and become the girl outside that i feel inside. i have let myself be hindered by a near-crippling shyness and an uncertainty as to what my next step should be.

Until just last week...

About a week ago, i met Mistess Cecila in a chat room. She sought a sissy to train online, and i the training. i don't know why, in a room full of sissies and wannabe gurls, She chose me, but i feel so grateful and fortunate. i am so unworthy of Her attention and consideration, and yet she takes the time and makes the effort to train me, not just to be a pretty sissy for an evening's amusement, but that i might be a girl wherever, whenever, forever. And all i have to offer Her in return is adoration, devotion, and obedience. If You are watching, Mistress-and i know that You are (giggle)- Thank You So Much... (curtsey)
Mistress has been, and will be, setting assignments for me to gradually 'force' me out into the world as a girl. (i am, of course, both terrified and exhilarated by the prospect.) She has decreed that i am to keep a textual and photograpic record of my completed (and failed) assignments via this blog. (giggle) i've never blogged before, or even kept a journal or diary, so i hope i'm doing this right...
i've completed a couple of assignments already, but i'm behind on my blogging, so i had better cut this intro off here, and get to work. Hope you enjoy following my progress in the coming days and months as much as i look forward to becoming the girl i've always dreamed i could be.
It begins...