You check your voucher book, and are frustrated to see this is the only department store in the mall offering a major discount on clothing. You'll save both time and money shopping here.
You wander over to the women's section as casually as possible, looking for something in your size that doesn't also look too feminine.
Eventually you settle on a white button-up blouse. It's free of fancy trim and has plain buttons, but its wide style of collar and particularly short sleeves are clear signs of its intended wearer's gender.
It's the best you can find, however, and you move onto pants. This is somewhat easier, as you find a pair of jeans that match your present waist and length. You grab a plain black belt from a rack and head into the changing room.
You're relieved to find how well everything fits. The jeans hug your hips rather tightly, but otherwise look androgynous. The blouse makes you look a bit more effeminate, but not in an overt way like your hair does.
You put your normal clothes back on, loose as they are, and go to find some shoes. Your plain white socks are still an okay fit, but your shoes are so floppy you're in danger of walking right out of them. You're pleasantly surprised to find a pair of dark blue gender-ambiguous trainers that fit your feet perfectly. Hopefully this is a sign of your luck picking up.
With a renewed sense of determination, you go to pay for the outfit. The cashier regards your baggy and shaggy appearance with a raised eyebrow, but says nothing. You pay, take the bag of clothes, thank her, and leave as quickly as possible and with the minimum amount of eye contact.
You find your way to another bathroom and rip the tags off the new clothes. You change as best as you can in the cramped toilet stall, and throw your old shirt, pants, belt and sneakers into the shopping bag.
You're very thankful that you decided to wear briefs today. As tightly as these jeans hug your waist, boxer shorts would have been very uncomfortable, not to mention noticeable. One small problem is the lack of room in the pants for your crotch. You manage to tuck it in as comfortably as possible, and hope it will be okay for the time being. The bulge between your legs, while visible, shouldn't be too obvious to anyone you pass by on your way out of here.
You exit the stall carrying the shopping bag with your belongings, and take one more look in the mirror. You grumble at the very feminine boy staring back at you. The face and posture are masculine, but everything else... Your body is too small and thin. Your shirt exposes a lot of your collarbone and its sleeves don't even reach halfway to your elbow. Your hips stand out thanks to the tightly-cut jeans. The only clear indications of your male status are the bulge of your crotch and the flatness of your chest. Your face is still definitely masculine, but even that has taken on a more ambiguous look thanks to your weight loss.
You're more anxious than ever to get your hair cut and find some way to gain your height and weight back. You storm out of the bathroom and continue on, dead set on getting back to the way you were.