Taking Colleen Out Clothes-Shopping

Colleen had actually been the one to suggest that we do boyfriend-girlfriend stuff together in the first place. It had come off like an idle idea, something she was proposing in case I liked it because she didn't want me to get tired of her and replace her with some other girl, but it lingered in my head. The girl I had been crushing on for so long now had no choice but to become my girlfriend if that's what I wanted... and it was. It was very much what I wanted. I had an erection just to the thought that I could make her go out on a date with me, as absurd as that was.

So I called her up. "Sam?" She asked, in a quiet, nervous voice, sounding almost like a mouse.

"I'm going to take you out tomorrow after school," I declared, without even asking about her opinion on the subject.

"Okay. Thank you," she said, and I could hear her fidgeting as she submitted to my command without hesitation. "For, for being nice, you know, and taking me out, I know you don't have to, since I'm your just future Pet if that's what you want me to be," she explained, in an increasingly nervous voice, her control over her mouth fading as her social anxiety flared to life.

"I want to take you out," I repeated. "I want to try acting like a real boyfriend." All the other girls I was fucking at this point - well, it wasn't the same as Colleen. She was my crush, and now she had to do whatever I told her to, and I thrilled a bit at that power as I ordered her around.

"Okay," she agreed quickly. "If it's what you want, then I'll do it."

"See you tomorrow," I said.

"L-love you! I mean, bye!" She hung up the phone suddenly - then immediately sent me a text:

Sorry! I just say I love you to my mom before I say goodbye! Please don't be mad if it was presumptuous or something!

* * *

When my arousal had declined down to something more manageable, and my upper head started to properly function, I realized that it was really shitty thing to do, to just force Colleen to go out on a date with me. I hadn't asked, just ordered. Sexy a thought as it was, I really liked her and wanted her to be happy - forcing her to do things just for my own sake almost certainly wasn't going to do that.

That's why, for our date, I decided to take her out clothes shopping. I had a big allowance, so I had plenty of money to actually go out to one of the nicer clothing stores, and she happily ran between everything on offer, from tube tops to bras to sweaters to corsets to fancy dresses to dress gloves, holding them up her body experimentally, checking each time if it was something I'd like.

Eventually, we had a truly massive collection of clothes, and Colleen headed into the dressing room with them - I helped her carry them in, hanging them up on the available hooks. The place was expensive, and part of that was that the dressing rooms were spacious, since a decent number of clothing items they offered were the sort that you'd want an attendant to help out with. It was honestly probably one of the most expensive places I'd ever been to - and if I hadn't been here for Colleen's sake, there was no chance I'd have been willing to spend the money.

"Which one should I try on first?" Colleen asked, as we finished putting all the clothes up. She chewed her lower lip nervously, and I looked over the options, trying to find something that was the most 'her.' Her style had really tended to emphasize her tits for pretty much as long as I'd known her - I remembered that since she started wearing tube tops and the like the day after I'd first commented on how big they were getting.

I finally settled on a rather sleek red dress, the sort which was designed in a complex criss-cross, making it cover her breasts but not her stomach, sliding around to a long skirt with slits that would show off her legs from the side. It was the kind that didn't allow for a bra, but that was fine with me. Colleen never wore them anyway.

I started to leave the dressing room, to give her privacy, but she clasped my wrist suddenly, then blushed and squeaked as she realized what she'd done when I turned around to face her. "U-um, you don't have to leave, unless you want to," she said, with a wet swallow. "I mean, you've already seen me naked, and, we're, being boyfriend-girlfriend? Is that too far?"

"It's fine," I said, leaning against the wall to watch her strip. She blushed and smiled, hurriedly starting to strip out of her regular top, making her large breasts bounced as she got undressed the rest of the way. There was a light flush to her whole body, a slickness to her sex, her nipples hard and perky as she gathered up her clothing. She was blushing and looking up at me as she quietly wriggled her way into the new clothes, making her tits bounce, that gorgeous body of hers slowly worming its way into the clothes perfectly right in front of me.

She filled it out beautifully, as she affixed the clasp at the back of the dress's collar, which served to help provide a place for the weight of her breasts to rest. The clothes might have been a mite too small for her, but even though I didn't want her having to wear something that didn't fit her right all day... well, seeing her breasts straining at the underside of the dress's top, looking like they might pop out at any moment... "L-let me see if it'll pop off if I move too much," she said, before starting to hop up and down in front of me.

I honestly have no idea if she was doing that to get a reaction out of me, but it certainly succeeded. Almost unconsciously, my hand went to my groin as I stared at those big, beautiful, bouncy breasts of hers.

The moment she saw what I was doing, her eyes flashed with eagerness. "A-ah, we should test other things about it," she said, and I nodded. "Like, does it feel good if you fuck my tits from below in it?" She asked, dropping to her knees in front of me and pulling down my pants a moment later.

This place was high quality enough that the clothing was all designed to be stain resistant. Pokegirls could squirt and squirt and would just drop their skirts at any time, so having something that was going to be able to just be tossed in the wash after getting cum and juices all over it and come out looking fine was important for everybody. They wouldn't have put locks on the dressing room doors and let you go in without an employee, if they hadn't expected things like this - so I wasn't too worried about us getting kicked out, as Colleen withdrew my cock, staring at it with an expression full of lust. I could almost hear as her throat bobbed and she swallowed - then she leaned forward, wrapping my cock in her mouth, sliding down to the base in a moment.

Her mouth was incredibly wet, as it engulfed me. She quietly adjusted her glasses, looking up at me from her position, her nose in my pubes as her eyes leered up at me. Her throat swallowed around my cock a few times, her tongue slithering back and forth on the underside of my length, drooling as much as she could as she held it in her mouth - then she popped back off, inspecting it, stroking it, shifting to have her mouth above it and drooling out as much as she could on my cock.

It was an unbelievably sexy sight, and part of me wanted to just started fucking her face right then and there, grab her braids and pound away. Instead, I patiently waited - this was Colleen's date, and we'd do it how she wanted to. I just reached down to softly pet her, and she smiled and blushed at that, this cute nervous look in her eyes.

Once she felt I was adequately lubed up with her spit, she shifted her body up, angling her dress so the underboobs teased at my cockhead. She took a deep breath, then started to slide down my length, her cleavage having already been tightly stuffed into the dress before. Now, all that pressure was brought to bear on my cock as she slid slowly, ever so slowly, down my length, really taking her time, making me groan softly at the pressure. Her heands pressed against her breasts, squeezing them still further around my cock, her perky nipples showing through the thin fabric.

I just let her work, enjoying the feeling. They were her clothes - if she needed me to do anything in particular to test them out, she could ask, and I'd do it.

"Is it good, Sam?" She asked, as her fingers kept up the pressure, her upper body sliding up and down in this gentle, methodical movement.

"It's great," I groaned out, and she smiled brightly at that.

She licked her lips at that point, glancing down and sliding my cock ever deeper into the valley of her breasts, until a distinctive bulge bloomed from the top. She leaned forward at that point, kissing my dick through the fabric, smiling as she saw and felt it twitch. "Do you want me to make you come, Sam?" She asked. "Would you like coming inside the dress?"

I thought about it for a second, but I decided that I didn't want to come too quickly, if she had more tests to do. I would be able to get it up a second time, a third, but we had a lot of clothes to get through, and there wasn't any guarantee this was the last time she'd want to try out something sexual in the outfits. "Do you, nn, want to do other tests?" I asked. She blushed and nodded quietly, pausing for a moment. "Let's do some, then. Change things up."

"Alright," she agreed, leaning up, popping my still spit-slick cock out from between her breasts, some of her drool now slobbering down the underside, along her stomach, an intensely lewd sight to my eyes. She turned around, pressing her hands against the wall, presenting her butt to me. "L-let's see how hard it is, to just, fuck me in this, without taking it off."

This particular dress's skirt reached all the way down to her calves, so I had to squat down a bit to grab it by the base; the front and back halves were pretty much entirely disconnected, so I could just roll it up past her waist. I was reminded, then, that she had gotten naked and not put on her panties, leaving her pink sex glistening right in front of me.

It was a very nice sight, the rolled-up dress and the gorgeous round ass in front of me. My hands went to her butt, squeezing and molesting the cheeks... and the dress promptly started to fall back down, unrolling along my forearms. I frowned, rolling it back up. "Hold this," I ordered her, and instantly she reached back to grab it, clamping the rolled up dress against her back and letting me molest her ass without worries.

"Is it sexy?" Colleen asked nervously. "Th-the dress I mean."

"It's hard to tell, because it's on such a sexy girl," I said, and instantly Colleen flushed bright red, a shy smile on her lips. I slipped inside her a moment later, and she let out a little pant as I did. She felt tight, and she looked like she was just about to come from a single thrust, which was definitely hot - so I promptly started to fuck her, and she started panting pretty much immediately, her cheeks glowing red until at last she came after less than a minute, a moan escaping her throat as her body thrashed.

In her thrashing, though, she lost her grip on the rolled-up dress, and it slid right back down over me, covering my dick, getting awkwardly scrunched between our bodies as I tried to fuck her. I pulled out at that point, letting it fall easily over her lower body, admiring her as the last few vestiges of her orgasm ran through her - then she spoke. "S-sorry, I was trying to keep the dress up, it just felt really good, Sam..."

"It's okay," I said, reaching over to caress her cheek. "It's why we're testing it, right?" She nervously smiled and nodded. "Let's try on something else," I said, looking around. The sooner she put on a new outfit, the sooner I could test out how her body felt, the closer I would be to actually coming. This was my thought process at the time, but Colleen didn't seem to mind at all, hurriedly getting herself out of the dress.

She quickly decided on a very nice version of the kind of sweaters she normally wore, with the exposed underboob and the long arms. She didn't even bother to pull on any kind of skirt or panties, as she knelt down in front of me, just sliding her breasts around my cock, the tip popping up from the top to the open air. She tried to lean down to lick it, and it took her a few seconds of work, even when I just buried my dick in those breasts of hers, my balls slapping against her ribcage in the process. Her tongue flicked against my slit, and she looked up at me nervously as she tried her best, grabbing her tits and trying to heft them up for a couple seconds before seeming to give up.

"Umm, it's too tight, it doesn't want to move up enough for me to suck on your head... it might just be the size though," she added quickly. "We could ask for a different size."

"We have lots of other things to try on," I said, again, motivated more by my desire to ejaculate than by any real thought to Colleen's feelings, but she blushed and smiled.

"Oh! M-maybe it'll be nice to give me a titfuck the other way," she said, popping off my cock to lie down on her back. My cock throbbed in the open air at those words, and I got on top of her, knowing the position she meant. I managed to slide my cock in under the tight fabric of her top, and then I slid easily down through the valley of her breasts, which still felt lubed up from her spit from earlier, despite her having changed outfits once now.

I could feel as Colleen's tongue slithered along my taint, my balls, my ass, rimming me when I was deep inside her breasts, then sucking on my balls when I slid backwards. Her hands were on her breasts, gently massaging my dick as I fucked them, and it felt really good, my dick threatening to explode at any time. My cockhead dribbled out some precum onto her stomach before she spoke up again, from under my butt. "Is it good for you?" She asked.

"It's great," I breathed out.

"D-do you want to try another outfit?" She asked.

"Not right now," I said, pumping my hips a bit faster now that I was no longer thinking about trying to drag things out for Colleen's sake. Colleen just hummed pleasantly and started to do her best to rim me as I fucked her tits hard, but obviously it was hard - I was constantly moving. She got my balls slapping at her chin or nose plenty, and each time she let out a little squeak of surprise, tried to shift to suck on them a moment later, then lost them as I kept on fucking away.

I came soon enough, spraying out hot cum all over her stomach, the stimulation sufficient to send semen reaching down to her thighs, pretty much just coating her lower body is several long, sticky strings of cum. I pulled out of her breasts, then, grabbing the hand towels that were provided with the dressing room, and dabbing up the whole region. She lay there, looking a bit dazed for a few seconds, then suddenly jerked to attention. "I can do it, Sam, you just came, guys feel lethargic after coming, r-right? So you can just sit down," she said, hurriedly.

I decided to do as she said, settling down on the bench as she hurriedly cleaned up her stomach and thighs with the hand towel I'd provided, and then leaning into it, taking a deep sniff, one hand absently trailing down between her thighs. It was an incredibly sexy sight, my cock soon absolutely at attention to the sight of my childhood crush now sniffing my cum while she played with herself, seemingly completely lost in the moment...

I decided to let her come at least once before interrupting her. The sweater top looked really nice, jiggling with her arousal, even as Colleen seemed to have just forgotten where she was or what we were doing here. I absently stroked my still-erect cock, and it was only once she orgasmed that she finally realized what she was doing. "A-ah! Sorry! Sorry! I really don't do things like this normally," she said, practically throwing the hand towel away from her like it was on fire.

"What do you mean?" I asked. Was she one of those girls who didn't masturbate?

"A-ah, never mind," she said, hurriedly leaning up. "Oh, you shouldn't have to stroke yourself when I'm here," she said, doing that kneel-walk hurriedly over to where I was sitting. Her eyes flicked over to a set of nice fancy gloves, the kind that closely followed your skin and reached up past the elbow, and she started trying to pull them on before realizing that her long-sleeved top was going to interfere. She squeezed herself out of that, her breasts bouncing deliciously. One of her hands started to absently stroke me as she tried to pull a glove onto the other hand using her teeth and gravity - it didn't work very well. It was a cute sight, seeing her struggle, the way her attention flicked between my face, my cock, and her arm as she tried to cover it up.

Eventually, she gave up. "Sorry," she said, pulling on the gloves quickly and then turning her attention back to my cock. "L-Let's see how it feels to get a handjob from these gloves!" She declared. They felt silky smooth on my cock, as she gently teased it for a few seconds, her fingertips brushing along the crown, sliding down to the base, cupping the balls, teasing the tip. It felt great, the gentle, teasing brushes, but soon enough she shifted to jerking me off - and that felt even better.

She had a certain lewd look in her eyes, as her attention slowly slid down to my cock. She leaned forward, her breasts seeming particularly large at this angle, gravity serving to exaggerate their size as her lips came closer and closer to the tip of my cock. She didn't start sucking, though - instead, she started to sniff, drinking in my scent and having a wild look in her eyes, as they rolled up in pleasure.

Did my cum really smell that nice? Maybe she had a cum fetish or something. It was pretty hot, seeing this secret lewd side of Colleen. "Play with yourself," I said, and being reminded that I was there made her jerk suddenly. "So you can see if the gloves feel good on your skin too," I told her.

"Y-yes, okay, Sam," she said, nodding quickly, one hand stroking me while the other slid in between her thighs. She gasped a little, eyelashes fluttering. "They feel good," she agreed, before falling back into her earlier fugue, sniffing at my dick as she wore a hazy, ridiculous look on her face and kept playing with herself.

Then I came, just splattering all over her face with another load of cum. She promptly came as well, moaning in erotic joy as I coated her with my seed. Her face became an intensely lewd thing, red from exertion but stained white with my seed, her lips parted as she sucked in deep, heaving breaths, her glasses rendered completely useless due to the splattering of two separate loads of cum on them. She didn't even bother to clean them off at first, she was too distracted with her own orgasm and the scent of my cum and everything else.

Part of me noted that I'd have a hard time getting through all the clothes, if I was coming for every other outfit - the rest of me was too busy admiring the way that Colleen drew up one hand to start scooping up my cum, feeding it into her mouth happily. My cum seemed to have helped her forget that I was here again, and she went back to being an uninhibited cum-drinking slut, one of the sexiest things I'd ever seen. I wondered if she'd be more uninhibited normally, if I put a blindfold on her? Maybe I could order her somehow?

Eventually, she cleared away the cum from her glasses with a hand towel, spending a few seconds blowing on them and repeating another brushing, until they were good as new. "U-um... let's see how all the bras feel for a titfuck," she said, and I just nodded in agreement, letting her pick something out quickly and pull it on, leaving her wearing just gloves and a bra - it was much sexier than if she'd been naked.

We tried out every single thing that we'd brought to the dressing room. The tight bras - how did they feel about my cock? Was a corset fun for a reverse titfuck, like that sweater had proven to be? How easy was this or that skirt or dress to get access to her pussy? (There were no pants at all, among the things she bought - she seemed not to like wearing women's pants, which was perfectly fine with me, since I thought skirts and dresses were sexier.) When my cock was taking its time to recover, she'd do something more soft and sweet, seeing how a top felt for me when she hugged me or clung to my arm, suggesting that I try groping her in this or that outfit so that we could both appreciate how nice it felt.

It had the secondary effect of getting me quickly hard again, of course. Then we'd try something really lewd again, until I ran out of juice and needed a recovery period.

The staff weren't upset at all, since I spent several thousand dollars on that outing. A lot of it was just variations on her 'standard outfit,' sometimes with an underboob-exposing t-shirt or camisole instead of a sweater, sometimes with a skirt that just barely managed to cover her ass. The kind of thing I liked seeing her in and she liked wearing.

I did buy her a really nice dress, similar in design to the first one she'd modeled for me, but with a skirt that didn't cover her thighs. She had asked, "Are you sure you want this one instead? I'll, I'll get a safety pin or a clip or something if you want, to hold it up, if it's the kind you like, don't hesitate just because it'd be a bit inconvenient for me! Or I could just learn to hold it right, I'm really sorry about-"

"It's great," I said, squeezing her ass cheek. "I like seeing your legs," I said, and she flushed bright red at that. "We got a whole lot of different outfits. Let's see how this one works." We found that it was easy to fuck her in it without any worries about the fabric bouncing around.