You start of hesitant but soon indulge your sister and yourself

After finally finding a parking spot you and your sister Gwen exits the car. As soon as you do Gwen bolts around the front of the car to you, all but trowing herself at you as she hugs you. "Oh my sweet little Amy, you have no idea how happy you are making your big sister." she laughs. Her happiness is contagious and you can't help but smile back at your sister. "Come on." Gwen says breaking heir embrace and grabs your hand. You allow her to lead you into the mall.

You start at one of the woman clothes stores. Gwen starts immediately picking out things while dragging you along while commenting on everything. You barely have time to notice what she picks. Finally you stop at a fitting booth and Gwen pushes you inside. Standing in the cramped booth Gwen smiles at you. "Now Amy, strip." She commands you. "shouldn't you be waiting outside?" You ask sounding somewhat meek. "No i need to help you with these things, operating a bra for instance is something that needs to be learned. Now don't be shy, i'm your sister after all, you can trust me." She says almost gleefully. You sigh and start stripping while your sister looks on. Finally you stand before you sister completely naked, your nipples hardening in the open air. Still smiling your sister takes in your entire naked form. "Well aren't you just the cutest, sexiest little thing Amy?" she comments shamelessly. You feel yourself starting to blush, feeling embarrassed by your exposure but at the same time you like having someone clearly interested and complimenting your body. "Now put these on." Gwen commands as she hands you a pair of white girly panties and a matching bra. You hesitate, this doesn't really feel like you at all. "I don't know Gwen." You say clearly hesitant. "Just put these on, if you don't like them we while try something else." She says like there is no big deal in you putting on women's underwear for the first time in your life. However you choose to indulge your sister. The panties are no problem and the actually feel nice and soft while fitting you really well, The bra however turns out to be a bigger hassle as you struggle with the clasp. "Um mind giving me a hand with this Gwen?" You ask feeling rather embarrassed at your ineptitude. "How come all boys struggle with this." Amy sighs as she helps fastening your bra "it's almost like you don't have to wear one everyday for your entire life." She continues teasingly.

Gwen turns you around and starts moving around your sensitive tits in you bra. "There, how does that feel." she asks when she feels happy. "Honestly it doesn't feel bad." You respond. "Good now look in the mirror" she says with anticipation. You turn to look in at your own reflection and get taken aback by what you see. The bra and pantie set although somewhat girly and plain compliment your body greatly. You actually think you look hotter in some way like this than when naked. "Well, do you like it now sis." Amy says with a mischievous smile. "Yes, they are great" you murmur still transfixed by the image of yourself. "Great now for the crowning achievement" Gwen says and pulls put a blue summer dress. "A dress, i don't now Gwen, underwear is one thing but i don't feel ready for a dress yet." you say very hesitantly. "Oh just try it on, you are going to like it i promise." She says sounding like she knows she is right and that you should stop questioning her. You submit and pull the dress over your head. You close your eyes as you adjust the dress not daring to look at yourself. "Oh Amy you need to see yourself." Gwen says sounding genuinely amazed. You open your eyes and look in the mirror, You gasp at your own image. You look beautiful. That word is probably the only way you could describe yourself. The Dress both hides and exposes your body in a great way. The color supplement you greatly You feel your movement being completely unhindered while you slowly start turning looking at your gorgeous form. Gwen Smiles at your reflection. "Now my sweet little Amy, Never doubt your big sisters advice again alright?" She says confidently. "I wont sis." you say as you almost start dancing in front of the mirror. "Good, now strip of everything, we have a lot to try on." Your sister orders and you excitedly follow her command.

You spend the whole day at the mall trying out clothing with your sister. At first you let Gwen chose but over time you become more involved in the picking process. As a guy you would have found a day like this to be **** of the highest degree. But now you get excited trying out new clothes and seeing what fits. You lose track of time as you and Gwen visits every store in the mall, trying on new. Gwen even takes you to a makeup session and starts instructing you in how to pick the right things for your skin. However since you don't have infinite money and time the makeup tutorial is only on an product presentation basis, but you seem to drink it all in still. Gwen is truly a font of knowledge on everything feminine you realize.

Having fully enjoined the shopping with your sister you can't help but start feeling tired as you have been trough every store while absorbing the many wisdom's of your older sister. "Just one more Amy then we will leave i promise." Gwen says noting your tiredness. During a short break between stores Gwen have had you change to the blue dress you bought at the first store, under it a you wear a cute bra and matching panties. "haven't we been to every women's store in this mall already?" You sigh. "Oh this is not that kind of store." She says as she leads you into a store named the baby emporium. You get a weird but familiar mix of feelings as you enter. The store seem to sell practically everything baby related a mother might need from maternity clothes, breastpumps too cribs. Walking trough the store you can't help but feel a bit scared for the future but also excited and a bit turned on. Every object brings a fantasy to mind. The maternity clothes makes you excited as you imagine how you are going to swell large with child. The nursing bra makes you imagine putting your hungry offspring to you milked filled teats as they greedily drink from your engorged nipples. Every thing in the store leaves you feeling more and more excited. At the baby clothes section you and Gwen nearly loose it. You both spend several minutes looking at the clothes while saying how cute everything is. At that moment all you want is a baby to dress up in all the cute little outfits. After a long while at the baby emporium You and Gwen manage to finally tear yourself from the store with a combined effort.

You make your way back to the car and back your things. You both continue talking the whole way about everything and nothing. You don't quite realize it but your bond with your sister has never been stronger and you have almost entirely given up on being a guy.