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Part 1

I had been planning this week for months. From the time my girlfriend let me know that she was going to have to go to Europe for a week in July for a fashion seminar I knew what I was going to do. My girlfriend Joy is a designer and often got to travel around the North America for her company in order to stay on top of what was happening in the world of fashion. However, she had never been to Europe and never away for a week. Her employer would pay for here trip but not mine so we discussed it, but I knew I was always going to tell her we couldn't afford for me to go with her. So once I had convinced her of that I had taken every effort to make this an unforgettable week for myself. I had been squirreling away some "fun money" in a secret account for some time and now it appeared that I was going to get my opportunity to have fun with it.

I have always been a diaper lover/cross-dresser. I felt that from the day I was born God had made a mistake and given me the wrong chromosomes. My "manhood" felt like a foreign object to me, a curse. I absolutely hated everything about being a boy growing up. I couldn't stand all the "macho" things that guys did; fighting, swearing, sports etc. I would much prefer to sit down and watch a beautiful movie and have a good cry. I tried to hide this side of myself from everyone, but of course your true nature has to come shining through at some point for others see. This didn't make me popular with the guys at school so I spent most of my teen years getting beaten up for being a "sissy". Now though, I was finally going to get a chance to at least for a week live the way I wanted to.

My days off rarely lined up with my girlfriends so I decided that on my days off I would go out of town to Hamilton (we live in Niagara Falls) in order to pick up the feminine items for my fantasy. I went into a discount department store in order to pickup some of the items I needed. I started towards the lingerie section but hesitated for a few minutes. Although I had worn female attire in the past, I had never bought female clothing and was feeling a bit apprehensive. I kept circling around for a what seemed like an eternity waiting for the section to be clear of women. Of course no matter how long I waited it never cleared. So finally I said to myself "nobody here knows you so what do I care what they think?" I now had the courage just to walk right up to the bra section. I wanted the most satiny padded bras you could imagine. In fact I wanted lots of them. I had measured my chest and knew that I wanted a 38C padded under-wire bra. They had a number of bras on display and the boxes of each right below them. The minute I touched one of them I immediately felt an electric charge run right through my entire body. I of course had felt bras before, but never knowing that this was going to be mine. It took me a few minutes to find the type and size I wanted, but I eventually did and quickly placed six boxes of them into my cart. I got a few stares from the women and one of the staff in the section but I didn't care anymore.

Next I headed over to the area with the slips. I quickly found some that would fit me and I put two of them into my cart; one half slip and one full slip. I then proceeded to the checkout. There were a bunch of men around and this intimidated me a bit so I hovered around the checkout area for awhile building up my courage again. Eventually I headed for the checkout. I had waited until one of the lines seemed small and headed for it. I started putting the items up on the counter and immediately felt the burning stare of everyone around me. Once the clerk finished with the lady in front of me she then started to ring up my items. The clerk to her credit didn't say a word out of the ordinary. She asked me if I had found everything that I was looking for and I said yes. She rang up all the items and once she had I paid and quickly as I could raced for the exit.

Of course they had a magnetic security system in place at the entrance. As I walked through I heard the words "Pardon us, but apparently we failed to remove one of the security tags from your purchase. Please check with our security personnel to have it removed". I couldn't believe it and I turned around to see a male security guard heading right for me. He asked me to place my purchases up on a counter that he was working beside and asked for my receipt. He started pulling all the items out of my bags and placing them on the counter, searching for the security tag. It was all he could do to stop himself from laughing. Everyone walking into and out of the store got a good look at what was going on. I wanted a hole to open up in the earth and swallow me up. I could feel my face and ears get flush from blushing and my heat was racing a mile a minute. It felt like a million butterflies had just flown into my stomach. Here was a guy with a bunch of dresses, bras and slips getting checked by security. Of course I heard the occasional chuckle from other customers. After searching all the dresses he couldn't find any of the tags so he paged for someone in lingerie to come to the security desk. I couldn't believe he wouldn't just let me go, especially as I had the receipt. I think he was just getting his rocks off embarrassing me as long as he could. After about five minutes a lady finally came. He explained to her what had happened and she said that sometimes the put the tags on the bras inside the boxes. So they started opening them and after the third one the found the tag and removed it. They packed up my goods and I was finally on my way.


Part 2

I placed all my purchases in the trunk and got in my car. Once I sat down it finally hit me; my heart still racing and my mind swirling. I had just bought women's clothing for the first time. I have never felt so empowered in my life!

I knew although I had saved up a fair bit of money, but there was no way I could afford to buy all new dresses for my fantasy. So I headed of for a Goodwill store. I had checked online before I headed on my trip in order to know where it was in Hamilton. I headed inside and picked up a cart and headed straight for the women's section. Fortunately the store wasn't that busy, just the one clerk and a grey haired lady checking out appliances. I had never purchased dresses before and had no idea what size I was. I knew however from observing other women's clothes that my best bet was to purchase skirts with elastic waistbands and longer sun dresses.

I sorted through what they had on the rack and found a fair amount of what I was looking for. I found a plaid skirt with an elastic panel in the front. I knew for sure I could wiggle into it if I had to. Next I found three other light summer type skirts that flared out at the bottom. I was always so envious of the women that got to wear these types of skirts. How free it must feel to be able to go outside wearing these light, airy garments!

I decided I also wanted some full length dresses and head for another rack. I quickly spotted a red, crushed velvet bridesmaid dress that to me seemed huge. I couldn't believe that any women could be that large but then I thought "yes even big girls go to weddings". The dress purple sating an had long narrow sleeves and an elastic bodice and flared out wildly. There was also a crinoline on a separate hanger tied with a twist tie on the same hanger as the dress. I assumed the crinoline must go with it. I knew that I could definitely fit into them. I couldn't believe my luck so I quickly placed them in my cart. I then picked out a couple of sun dresses and made a beeline for the checkout.

I started placing my purchases on the counter and the clerk had a stunned look on her face. After a few moments she asked me "Are these for you?" I was taken aback for a moment, not believing that she would ask me that. A million thoughts ran through my mind; what kind of lie could I come up with to tell her? But in a moment which to me seemed like an epiphany I simply said "Yes, they are!"

She looked at me for a moment and said "I think that's sick! I think you're sick!" I was dumbfounded. Unknown to me the grey haired lady who had been shopping there had come up behind me a said "Never you mind missy! It's none of your business what anybody chooses to wear or likes to do! I suggest you keep your comments to yourself or I will have to speak to your manager about how rude you are to your customers." The clerk looked down at the items on the counter and started ringing them in. I turned to the lady and said "thank you." She said "Dear, it takes all kinds to make up this world and if you or any man wants to get in touch with there feminine side, so be it".

I could not believe it. As I headed out of the store I was happy to know that at least there were at least some people out there that understood what I was going through! I got in the car and quickly headed for home. Once home I took all my purchases and took them into the attic. The attic was kind of rough and was full of cobwebs and spider webs. Joy was afraid of spiders so I knew this was the perfect spot to stash my treasures.

Part 3

Eventually the day was at hand. Joy's flight was to leave at 8:00 am from Pearson airport. I thought this was absolutely perfect. I had been doing some research online for adult diapers and had found a store in Mississauga called "Diapers Direct". I had called them to find out that they sold adult diapers and found out they did. Now I had bought adult diapers in the past, but thought that perhaps they would have something new and exiting to offer. So once I had seen Joy off I quickly dashed for the car and headed for Mississauga. I had a little difficulty finding the store, but eventually did. My experiences buying women's attire must have had an effect on me as I didn't hesitate for a moment to head inside.

The store front was very small but it was diaper heaven. From floor to ceiling were shelves stuffed with every type of diaper and undergarment imaginable. There were baby diapers, training pants, youth diapers and pull-ups and of course adult diapers. There was a man already in the store talking to the owner. The owner was talking to him about belted undergarments. The man stated he was looking for something for his mother. I couldn't help think to myself; is that was the truth or was this guy just too embarrassed to say they were for him. The owner gave the man a couple of samples and told him to have his mother try them to see which ones she liked better and come back afterwards.

Once the gentleman had left the store the owner turned his attention to me. Right off the bat he asked me "Are you looking for something for yourself of someone else". I didn't even hesitate and told him that I was looking for nighttime diapers for myself. He asked me what I had used before and I told him I liked Attends. I had tried a few different types of adult diapers before, but liked the Attends best because they felt most babyish. He said, that although they may be alright for daytime use, they certainly would leak overnight. He pointed me to some Tena brands and some Prevail brands of overnight diapers. He said both work equally well but he said most of his customers preferred the Prevail full-mat overnight diapers because they were more inexpensive per diaper and were very absorbent. He worked out a price for me a said that for a case of 72 it would be $99.99. I asked him if he sold Attends and or rubber pants. He stated the he didn't so I asked him to ring up my diapers and I headed out of the store with my purchase.

Part 4

Now prior to my trip I had devised a backup plan if Diapers Direct didn't sell the Attends. I knew from going into a local pharmacy in Niagara Falls that a certain chain did in fact sell the Attends diapers, but only at their "Home Healthcare" facilities. I looked up the one for Hamilton and called them. They stated that indeed they did carry the Attends diapers. So on the way home I stopped in. Inside they had a whole section dedicated to incontinence. I quickly spotted the Attends large diapers and picked up a bag of 18. Then I started to look through the various incontinent pants that they sold. As I was doing so a clerk came up to me and asked if I needed any help. I swallowed my pride and stated that I suffered from enuresis and needed some overnight protection. She seen the Attends I was holding and said that if I was going to us those for overnight that I would definitely need incontinent pants for extra protection. I asked her for her recommendation and she asked me if I knew whether or not I was allergic to latex or not. I said "I am not sure, I don't think so". She said "Well, I would recommend you don't take any chances and use rubber pants. These ones here are natural gum rubber and should not irritate you even if you are allergic to latex." I looked at them longingly and said "how do I know what size to buy?" She asked me my waist size and handed me a pair and stated "These will work perfectly for you."

She took me to the cash register and rang up my purchase. I now had almost everything I needed. Once out of the store I headed quickly to a local department store and purchased a large pack of Pampers size 6 diapers. I had experimented in the past and found that if you used two or three of these for liners inside your diapers that it made them feel bulkier and more baby-like. Now I had everything for my plan.

I headed for home with a feeling of ecstasy! I was finally going to get a chance to live out my sissy fantasy!

Part 5

Once I got home I couldn't wait to start my fantasy. I brought all my items in and the first thing I did was to call into work and leave a message that I wound not be in tomorrow or even possibly the next day due to the fact that I had the flu. I now knew I had at least two days all to myself in order to have fun! I rushed up to the attic and pulled down all my prior purchases and brought everything into my bedroom. I didn't know where to start so I decided to lay everything out and formulate a plan. I took all the bras out of their boxes and placed them in a pile on the bed. Next I took all the dresses out and laid them down from the smallest to the largest along with the slips. Then I took out one Attends diaper and six of the Prevail diapers and three of the Pampers. The last item was the rubber pants. I then went to the basement to grab a couple of rolls of packing tape.

The first thing I did was take the three Pampers and took a pair of scissors and cut of the tapes and wing section on the top and bottom of the diaper, leaving just the middle section. It made the diaper look more like a pad then a diaper. Once I had all three cut I then stripped naked. Once I had all my clothes off I took all three Pampers and placed them on my crotch. Of course there was nothing to hold them in place so I had to close my legs to hold them in place. I minced my way over to the Attends diaper and picked it up. I then went over to the wall and leaned my back against it with the back of the Attends diaper against the wall. Carefully I pulled the front of the diaper up through my crotch making sure that the Pampers stayed where I wanted them. I did up all six of the tape tabs, readjusting them to make sure the diaper was good and tight. The diaper already felt very bulky but I knew I was far from done. I poked a hole in the crotch of the Attends in order to allow any flow to move on through to the next diaper as I knew I was going to be putting on all six of the Prevail diapers. Slowly I proceeded to diaper myself with all six, each time poking a hole through each of the crotches except for the last one. I could not believe the bulk between my legs. I tried bringing my knees together but couldn't even come close. The bottom of the diapers ended right at my knees. I tried to touch myself through the diapers but I couldn't even feel a thing. It was all I could do to get the last one taped up. To make sure the diapers wouldn't move I took one of the rolls of packing tape and started taping it around the waist of the last diaper. I sucked in my gut as hard as I could and wound the tape snuggly. Once I had gone around about four times I took the scissors and cut the tape.

Now I had known from previous diaper experiences in the past that no matter how good an adult diaper to buy, when you lay down they always leaked at the waist overnight. So I had come up with a plan. I took two more Prevail diapers out and cut them the same way I had with the Pampers, taking off the tapes and the wings. I then placed them on the bed side by side to that two of the waist sections lined up. I then took packing tape a cut a few pieces and taped the two waist sections together making one very long looking diaper. I took this contraption and wrapped it around myself at the waist. It was plenty long enough to go around almost one and a half times. I positioned the bottom of it to cover the waist area of my diapers and the top just below my nipples. I grabbed the packing tape and carefully wound it around the waist diaper about six times nice and securely. Once I felt it was in place I then grabbed the rubber pants and pulled them on. Of course the only came halfway up the diaper, but I thought they might help leaks around the leg openings. I now had on the biggest diaper I have ever worn. It was all I could do to move my legs.

Next it was time for the bras. One by one I took them out of the box and put them on. Each one I put on made me feel more and more like a real woman and that I had real a real bosom. Once I had the sixth one all I stopped to look in the mirror and admire myself.

Now it was time for the slips. I grabbed the half slip and stepped into it. There was not much of my legs left exposed from the diapers, but what area were soon felt the satiny finish of the slips. I was in heaven. I pulled the half slip up and over the bulk of my diapers. Once in place I grabbed the full slip and slipped it over my head and pulled it down over my legs. It ended right at the knees.

I decided today that I was going to wear my bridesmaid dress so I next had to put on the crinoline. I pulled it down over my head and positioned the waist at my hips. It was a bit tight, but I managed to get it in place. I then cinched up the drawstring to lock it in place. It was now time for the bridesmaid dress. I took the bottom of the dress and pulled it over-top of my head. It took me a while to work my way up to the sleeves and stick my arms up through them. Slowly and carefully I pulled the dress down making sure not to rip it. Once the dress was at my waist I had to work the bottom out and over my crinoline. It took quite a while as each time I moved it pulled on side of the dress up and down. I could believe how wide it was at the bottom. I knew I would have trouble getting through doorways.

Once everything seemed in place I stopped to admire myself in the mirror. Other than my head, I looked like a bridesmaid. I began to swirl around; a difficult task given the bulk of my diapers. As I did so my crinoline swished and swirled. I felt like I was on cloud nine.

To be continued.

By BabyJenn

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