NSFW Author

If I wanted to become Samantha, I needed a complete new wardrobe.

I had become convinced that I would spend at least a year as a woman and I certainly couldn’t spend it wearing my old clothes.

I had no idea how to shop for woman’s clothes so my mom offered to take me to the shopping mall.

Before leaving, she went upstairs with me to measure my breasts. I had seen plenty of them inside and outside of bras, but I still had no ideas on how to measure them.

I was hesitant to remove my shirt in front of my mother, but she insisted I needed a proper bra and that without measuring, there was no way to make sure I would get one.

I shamefully removed my shirt and my mother stoically took two measures of my waist. One right under my new breasts and one passing right over my nipples.

She announced that the two measures were 33 inches and a half and 36 and a quarter, which translated to 34C. I was surprised to learn that the C simply means 3 inches.

I’ve always had as a guy a problem figuring exactly how cup sizes were determined. I knew that AA meant tiny, A means small, B meant medium, C big and D even bigger, but I never knew that these simply means 0, 1, 2,3 or 4 additional inches.

In a way, it was humbling. The big breast only had 3 inches of additional circumference than the small ones.

After I put my shirt back on, she proposed we start at Wall Mart to get some underwear and casual wear clothes.

We talked and decided to actually visit two of them. At the first one, I would get panties, a bra and one set of clothes which I would use to shop at the second one.

Panties were easy to find. I simply took two bags of white panties, both a high cut briefs and a bikini brief type. It’s when we arrived at the wall of bras that things became weird.

Guys have two basically three choices of underwear: boxers, briefs and boxer briefs. I already knew that girls had many types of panties but I was flabbergasted at the vast number of bras available.

Of course, even though most of the girls I dated had worn elegant bras when it was time to get physical I had occasionally seen regular day to day bras. This didn’t prepare me to seeing the aisle however.

There were dozens of basic types ! Front clasp, backless, sport, convertible, push-up, underwire, wireless and those are just those I remember !

My mother announced that underwire bra procure more support by that not all woman would wear them so she recommended a normal plain and simple threadless one which would irritate the least.

I tried a few pairs of jeans and settled for a low rise size 3 pair of jeans which fitted nicely on my nice long legs. Damn it, I was turning myself on !

I also bought a pink t-shirt which proclaimed me a diva. Hey, it’s not like I had the chance to wear pink in the past !

As soon as we left the Walmart, we stopped at a restaurant so I could change in the restroom. I almost entered the men’s room by accident but my mom was there to help me.

I must admit that my new clothes fitted my frame a lot better and that I was relieved to have some sort of support for the jugs I had been carrying all day. I almost regretted having fantasized about bra-less women !

Our first stop in the second Walmart was in the shoes section. I insisted on getting a pair of running shoes but my mom also got me a nice pair of sandals and a black suede pair of shoes with a mid height heel which was small compared to the other shows but still much higher than I ever wore.

The rest of our shopping procured me additional bras, pants and t-shirts as well as a few nice blouses. I even got three skirts and tried a few dresses but ended up buying only one of them. I wasn’t ready yet for that…

We did stop at the perfume section but I already knew which one to get: the same one that Anna wears. My nostrils of a man had been locked years ago on her scent and I even had the guts to give that same perfume as a gift to my subsequent girlfriends.

We finished out ladies day out at a lingerie store where my mother insisted I get at least two pairs of matching bras and panties, one nightie and a few pyjamas which fitted my new frame.

I obviously went for the styles that I had liked as a boy, preferring black over pink, and sheer through over solid and I surprised myself at not being ashamed as all at how sexy I looked.

Our total spending for the day well exceeded 500$ but my mother insisted it was worth every penny.

I hugged her as we were leaving the store which even surprised me, as I hadn’t done so for years. Perhaps my feminine side was coming out…