Clothes shopping

The next morning, the movers finally show up with all of your belongings. Since Kaitlyn’s only shirt is covered in cum now, she wears one of your shirts while the movers are unloading everything from their trucks. After a few hours, everything is inside the house and you’re all moved in.

Kaitlyn finds the box with her shirts in it and takes off your shirt to change into one of her own. She looks through the rest of the box, inspecting the shirts thoughtfully. She heads downstairs to find you on the couch in the living area.

“Hey, I was thinking. Would you like to go to the mall today and get me a bunch of new clothes? Ones that are more like that red one you got me? And maybe a couple that are even more skimpy than that?”, she questions, already knowing what your answer will be.

“That’d be great, baby! I have a few things in mind already”, you reply enthusiastically. In truth, you had a LOT in mind. You have been fantasizing about this for years. Even so, you know you have to limit yourself a great deal so that Kaitlyn can be slowly introduced to the slut life you wish for her to live.

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Heading to the mall and going into the first clothing store you find, you head to the women’s section. As if it were meant to be, one of the first tops you find is very similar to the red one you gifted Kaitlyn and is exactly what you had in mind. It’s the type of top that is perfect for slowly getting used to showing more and more skin, if that’s your goal. This top is black, a couple inches shorter in length which will expose even more midriff. The neckline scoops down much further, enough that it would show off the entirety of Kaitlyn’s cleavage and most likely show a little bit of the front side of her breasts as well. Showing interest in it, Kaitlyn stands by your side and looks at it with you. She bites her lip and makes a nervous looking face, clearly unsure about this shirt. You pick it up off the clothes rack anyway, suggesting that she at least tries it on.

Continuing to look around the store, you find a few other pieces of clothing you think Kaitlyn would look great in. One is a light green dress with thin shoulder straps, and doesn’t seem long enough to go reach Kaitlyn‘s knees. The other two things you find are two long sleeve tops that are once again similar to the red and black tops, but both of these are even more revealing. One is light blue with a very wide V cut neckline, almost completely avoiding the shoulders. The second top is white and has a deep U cut neckline. Both tops are much shorter in length than the red and black tops, barely meant to reach below the breasts. Kaitlyn‘s entire stomach would be shown off in these shirts and a lot of cleavage would too. You can’t help but imagine her turning heads and attracting eyes if she were to wear these in public. You feel your pants start to strain as your dick comes to life at the thought.

Again standing at your side admiring the clothes, Kaitlyn looks even more nervous about the dress and two tops.

“Oh my god, those are skimpy! I’ve never even considered buying anything like those in my life! I’d curl up in a corner if I had to wear those in front of other people!”, she says.

“Baby, you’re going to have to get used to wearing clothes like this if you want to explore any further into being slutty. Let’s at least try them on here. No one else will see you. If we decide to get them, you won’t have to wear them just yet. We can stick to the black top and keep moving as slowly as you’re comfortable with”, you comfort her.

“Okay, fine. Thank you”, she says, actually finding that agreeable.

Picking up the dress and blue and white tops, you take the four pieces of clothing over to the dressing room. On the way over, Kaitlyn gets distracted by a phone call and walks away from you. You decide to keep looking around the store while you wait on her. Thinking it’d be a good idea to get a variety of new types of clothes for Kaitlyn, you head over to the bathing suit section. Options galore, almost the entire stock is full of things Kaitlyn would consider extremely slutty. As she only wears one piece, conservative bathing suits, the mostly bikini options would almost certainly be too much for her at this stage. You manage to find a couple with more coverage area than the rest, and you add them to the bottom of the pile of clothes in your hand.

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Kaitlyn returns from her phone call a couple minutes later, finding you wandering. Handing the pile of clothes to Kaitlyn, you manage to hide the bikinis tucked under your arm. She heads inside and starts changing. It only takes a couple of minutes and you hear the door click open.

Kaitlyn slowly opens the door and takes a couple small steps out of the dressing room, not wanting to risk being seen by anyone else just yet. She’s wearing the first top you found, the shorter length black one. She looks incredible. The shirt is quite tight, pushing her breasts upwards and squeezing them together more than most shirts would. This makes her cleavage even deeper than her already big breasts normally present. You know she’s wearing a thin cloth bra with little padding, as you saw her getting dressed this morning, and you realize its a good thing because if she had worn a thicker bra, the outline would be clearly shown through the tight shirt and would most likely be sticking out from the neckline, which Kaitlyn would not be comfortable with yet.

Kaitlyn is looking down at her own chest, obviously noticing how much the shirt is assisting her in presenting her beautiful round breasts. She adjusts the top slightly, just to get it more comfortable, not as an attempt to cover herself up. This adjustment adds a wiggle to her movement, making her pushed up breasts wobble slightly, expressing their naturalness. Kaitlyn looks up at you and finds you mesmerized by the sight, unable to divert your eyes from her tits. Unlike when she caught you looking in the car last night, she doesn’t tell you to stop or cover herself up.

“Do they look good?”, she asks, clearly meaning her breasts.

“They look incredible, Kaitlyn. YOU. You look incredible. Wow.”

Giggling at how much you seem to be enjoying this, she does a little spin for you, putting her arms in the air. The spin gives you a great look at her ass too, filling out the tight jeans she’s wearing quite nicely. This reminds you that you should also look around for some sluttier leg-wear. Once again, her breasts wobble as she stops moving. You notice the hem of the shirt has moved up even more from her raising her arms, so even more of her stomach is exposed. Kaitlyn feels the shifting of the shirt and quickly pulls it back down into place. Pulling a bit too hard, she pulls the shirt too far. Even more of her soft globes are exposed and you can see the top line of her thin tan bra. She embarrassingly corrects this, starting to blush as usual. She’ll have to be careful with her movements when wearing this shirt if she doesn’t want to show off too much.

“This one’s definitely more slutty than the red one I already have, but I think I can handle it. I have to admit, my own jaw dropped a little bit when I saw how good I look in this in the dressing room mirror. And I know how much you love when I wear push-up lingerie, with how much movement they add to my already jiggly breasts.”, she says, laughing at the thought of how much you love her tits. She has never completely understood the fascination, but after seeing herself in the mirror in this top, she understands it just that much more.

Returning to the dressing room, she changes once more. Coming out each time to give you a look, every time the door opens you see more and more skin. First changing into the blue top, The wide V neckline shows a small amount more cleavage than the red and black tops, but mostly exposes more of Kaitlyn‘s shoulders. The “shoulders” of the shirt wrap around the top outside part of her arms, meaning she has to be careful not to tuck her arms too far into her body or the sleeves will fall down her arms. She’s not too comfortable with this shirt, but doesn’t say no to it.

Changing again, she comes out in the white top. The U shape neckline drops very low, almost to the middle of the front of Kaitlyn’s breasts. The majority of her chest is exposed. Because of the lack of length of the top, there is only about three to four inches from the lowest point of the neckline to the hem of the shirt. Her tan bra is peeking out from the neckline once again, even more than before. If she were to wear this in public, she’d have to wear a bra that she fully expected to be seen by others. The shirt isn’t tight overall, so it doesn’t push her breasts up like the black top, but its still more revealing. The hem of the shirt wraps snuggly around the underside of her bra and breasts, providing no wiggle room. If Kaitlyn were to lift her arms any amount above her shoulders, the shirt would ride up her chest and expose her bra from underneath. Stunningly sexy, you think.

“Um… this one is a bit much, don’t you think?”, she asks, expecting you to agree and provide some sympathy for how uncomfortable she’d be wearing this in front of others.

“No, it’s perfect! I mean, you don’t have to wear it in public just yet, but I think it’s amazing! This top is a great example of what I fantasize you wearing on a regular. Of course, I still fantasize about you wearing sluttier and sluttier clothes, but even if you’d only be comfortable going as far as this shirt, I’d be the luckiest man in the world!”, you explain, not giving her what she expected.

Kaitlyn can’t hide her smile. Seeing how much you’re enjoying her being naughty is quite funny to her, and it’s slowly making her more and more comfortable with the whole thing. Even if no one else ever saw her wearing these clothes, just your reaction to her in them was enough to make her want to keep doing it. She’s at the comfortability level now that she probably wouldn’t ever wear anything more conservative than the red shirt from last night, even if she were to back out of this fantasy of yours.

She turns around again and heads back in to the dressing room to try on the last outfit, the green dress. It takes longer to change this time.

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“Babe! I don’t know about this one. I think this is way too much for me! It shows about the same amount of my chest as the black top, but its very tight around my ass!”, she complains, still inside the dressing room.

“Well, don’t hide that from me! Let me see! No one else is around out here, the store is empty!”, you encourage.

The door to the dressing room opens slowly, Kaitlyn peeking through the crack. She finally builds up the courage to walk out after seeing your expecting expression. The dress looks fantastic. Not very fancy, its an every day type of dress. One that typical college girls would wear. The length of the dress is shorter than you imagined, only coming half way down Kaitlyn‘s juicy thighs. Not concerned about the cleavage part of the dress, Kaitlyn nervously turns around. Sure enough, the dress is much tighter than you expected it to be when you picked it off the clothing rack. It shows off Kaitlyn‘s curvy and plump ass incredibly well, sticking tight to the outside curve. She moves slightly and her ass bounces wildly. You’ve always known she has a fairly big and bouncy ass, but because she mostly wears jeans or pants that don’t emphasize her ass, you’ve only seen her ass this jiggly when she’s naked. Its a completely different, teasing enhanced perspective to see it being supported by a tight dress. Its as if the dress is encouraging her ass to bounce more than usual.

Kaitlyn reaches around, feeling her ass in the dress with both hands. She tries to pull the bottom of the dress down further to cover up more of her legs, but it doesn’t budge. She tests the dress by bending forward, wanting to see how far it would ride up her legs or ass. Giving you a dreamy view of her ass, the dress tightens even more, adding an even sexier outline to her curves. The dress rides up some, exposing another few inches of her thighs, but there’s at least 4 more inches before the very bottom part of her ass would even consider being exposed. Satisfied with how much it shows off your gorgeous girlfriend, you wish she’d wear that out of the store. You know she wouldn’t dare, though. Not yet anyway.

“Do girls actually wear stuff like this? How are they not concerned their ass and panties will be on full display?”, she questions with genuine curiosity.

Laughing at her innocence as usual, you find it hysterical that she’s asking a question like that in a dress that doesn’t even come close to showing any part of her ass or panties. Not close by your standards, and not close by any experienced slut’s standards either.

“Yes, Kaitlyn, a lot of girls wear dresses like that and shirts that show off way more than the ones you've tried on today. Believe it or not, a lot of girls enjoy dressing this way, because they find it naughty and sexy just like I do. They enjoy showing off. Not all of them want to expose their ass or panties, but some do. The sluttiest of the sluts do.”, you explain.

Kaitlyn seems to believe you and stands back upright. Asking what you think of the dress, you answer as expected. You know she won’t wear it for awhile, but you’ll go ahead and buy it. Maybe she’ll be encouraged to wear it on her own if she sees it in her closet every day. Kaitlyn goes into the dressing room for the last time to change back into her regular clothes. Knowing you’ll buy the dress even if she says she won’t ever wear it, she doesn’t even try.

Deciding it’d be best to wait until Kaitlyn is more comfortable with wearing revealing clothes before you go shopping for skimpier leg-wear, today’s shopping is completed.

Heading to the registers, you somehow manager to distract Kaitlyn by the jewelry section, which she isn’t normally interested in, while you go pay for the clothes. Scanning and bagging everything you picked out, including the two bathing suits Kaitlyn still hasn’t noticed,

As you’re about to finish, Kaitlyn walks over to you with a few pieces of jewelry in her hands. A couple fancy pairs of earrings and a few various necklaces in hand, she checks with you to make sure its okay for her to buy them. You approve, noting her slightly changing interests in her appearance.

Leaving the store and driving home, you bring up the idea of buying skimpier leg-wear in the future. Not mentioning any specific types, Kaitlyn is nervous for what you have in mind for her, but agrees that you should wait until she’s more comfortable first.

Very happy with Kaitlyn‘s progress towards your biggest fantasy, you remember that it’s only the second day of the journey. She has gotten comfortable with where she’s at quicker than you had ever expected, but you know there’s still a long long way to go until the farthest limits of your fantasy are reached. For now though, you couldn’t be happier.