Finding the Perfect Fit Pt. 09

Thursday Afternoon

It snowed last night and turned the campus into a frozen fuckfest, resulting in fender benders in every direction. Thankfully my Dad taught me how to drive in everything but the vacuum of space and as long as I went slow, it would take a truly fucked road to stop me. Which was good, as I had somewhere to be once classes let out.

While I didn't live in a huge city, it was still big for the state and had options. I'd been here my whole life here and knew it pretty well and there was a certain place I remembered seeing every so often. My memories of where it was were vague but once I searched around online, I found out it was still doing business.

Braving the snow and cold, I drove to a slightly shady part of town and found the place. Parking, I looked around, seeing bars over the windows and only one other lonely car in the parking lot, the neon "OPEN" sign dying the snow about it red.

Checking to make sure my wallet was secured in a pocket and that I locked my car, I plunged into the cold and headed inside. Thankfully it was warm but all kinds of things instantly demanded my attention, me unbuttoning my coat while looking at what was on offer. A manikin was standing right in front of the doorway, decked out in the shortest miniskirt I'd ever seen along with stockings and had a pair of handcuffs hanging from a wrist.

"I'll need to see your ID please." To my right was the check out counter, a bored woman about my age sitting back there. Digging my wallet out, I showed my driver's license to her and got a nod as she gave it back. "Let me know if you need anything."

"I'm gonna look around first." I was a college student so visiting a sex store at some point was sort of a given. Most of what I saw in the first few isles was junk: dirty games for bachelors and bachelorettes, crude gag gifts, flavored lubes that I promised to come back to and a light smattering of fetish gear. A bunch of costumes for Halloween were marked down, quite a few maid outfits calling to me but I tore away to the main reason I was here.

An entire wall of dildos. All sorts of colors, shapes and sizes, some that looked far too big and others of odd designs. It was overwhelming and I stood in silence, beholding this sight.

Finally, my eye caught the other half of what I was looking for. Walking over to a smaller display, I looked at the assortment of straps ons. They all looked similar, like a hardcore pair of panties with straps that went about the waist and each leg but had nothing for the back. The fronts had O-rings that a dildo fit into, looking simple enough. Checking the price of the one I'd been looking at made my breath catch, as eighty bucks wasn't going to happen.

Putting that back, I went to the bored attendant screwing around on her phone and prepared to ask about what Jamie seemingly wanted.

"Hey, my boyfriend and I wanna mess around with a strap on but I got no idea bout any of this. Got any suggestions? Or advice?" The woman, in a sweater with short dark hair, got up and joined me beside the wall of fake dicks.

"Yeah, pegging's gotten popular lately so we've had to study up." Thanks to school, when she started talking next my first impulse was to take notes. "Have you done anything back there before?"

"Uh, just some dry humping." Probably for the best that Jamie wasn't here to melt down at admitting this to another person.

"Okay, the main things is to take it slow, relax, and communicate. I'd suggest this one to begin with, it won't fall apart unless things get really crazy. It's what my girlfriend and I started out with." The box she handed me was sixty dollars and came with two dildos, a small, thinner one and a bigger, more realistic six incher. "And please, please! Make sure you have enough lube! I'll double check to make sure it's the right kind for toys."

Looking at the shape and size of the smaller dildo that came in the package, I imagined showing Jamie that and didn't see it ending well. It wasn't big compared to him but still, big for where it was going.

"Do you have a more beginner friendly uh... Thing?" Some of those dildos could be used as weapons and if I was questioning them, Jamie would probably run screaming.

"Yep, butt plug!" The happy way she said that nearly broke me but I kept the hysterical laughter bottled up. A small box was handed over, the picture on the front a smiling woman in a bra and holding what looked vaguely like a Christmas tree but it was all smooth and pink. There was a cone that flared out, then a much slimmer trunk came out the bottom with a flat, equally flared base.

"You lube up this part and slip it in." She pulled the package open, her tone that of my teachers, explaining in a practiced manner. "Keep it in there for five, ten minutes and it helps loosen things up. Then pull it out slowly, add more lube and go for it with that!" Made sense to me and hopefully would to Jamie as well. She put the butt plug back into the box and handed it over. I grabbed another one, making sure that my promise of fairness would be met.

"What lube would you recommend?" Arms full of perversion, I watched the woman browse for a few seconds before asking what flavor I liked best. I answered cherry, as it was hard to go wrong there. With that, I went to the counter and she started ringing things up, the total higher than I would have liked but still coming in under three digits.

"The best part about this is if your boyfriend wants to spice things up or get something bigger, you can always come back and get another dildo. Long as it has a base, it'll fit into this." I processed that while punching in my pin code into the card reader.

"Does that happen often, wanting something bigger?" I mean, I knew size wasn't everything but the wall of dicks showed that some people seemed to think otherwise.

"Of course." Her tone made it clear she found my question stupid. "My girlfriend and I upgraded once and have been wanting to try something new." She shrugged as if was no big deal, and it wasn't, but the idea had bit down and wouldn't let go.

"I mean, is it common for guys to want something bigger?" Jamie did have a nice ass and the thought of me controlling something going in there made that always lurking inferno stir, the immense heat already awake from being in this store and now ready for action. The chuckle from the woman behind the counter got my attention, her coy expression paired with sharp, knowing eyes elevating average features to savage beauty.

"Depends on the guy." Even her voice changed, becoming deeper yet more playful as she continued. "Some just don't like it. Those that get over the social stigma and all that shit, well, they usually end up really, really liking it." I became aware of a bead of sweat rolling down my cheek and wiped it away, hanging on her every word. The manikins showing off slutty fashions could have come alive Silent Hill style and I would have been rooted to this spot, listening to what felt like forbidden wisdom.

"I've had plenty of girlfriends and wives come in to pink up something to screw their men with, just like you are now. I've started offering a gift card to any guy who has the balls to pick out their own dildos but no takers yet." I gave a semi-sane laugh, burning up thanks to my coat, the store's heater, and my own rising need. She leaned forward, elbows on the counter, a knowing smile born from selling a city it's fantasies. "Judging by what they're buying, I'd say there's quite a few guys finding out they've been a size queen all along." I'd never heard that term before but it was easy enough to figure out the meaning. Was Jamie one of those, a 'size queen'? Even thinking those words in the same line of thought as Jamie made me shudder.

Leaning back, the cashier took on a more causal, instructing tone. "Talk with him beforehand, make sure he knows it's gonna be uncomfortable at first, even hurt a little. But once it's all the way in, well... If he likes it, you'll know." With that same fetching smile, she bagged my sex toys and lube in a plain brown bag and handed it over. "Good luck and I hope to see you again." I nodded, drenched in sweat from head to toe and got the fuck out of there.

The cold slap of reality, the dim gray of the concrete parking lot and a feeble excuse of sunlight dribbling past heavy clouds brought me back somewhat. Getting in my faintly warm car, I fired it up and cracked the windows, flicking on the radio. Guitar and drums pounded out as I laid shaky hands on the steering wheel. Shrugging my coat back, I took deep breaths of frigid air before finding a napkin in the glove box and slowly wiping sweat from my face.

I'd just bought something for the express purpose of fucking Jamie. Well, except for one of the butt plugs, which I was going to be getting familiar with. But the cashier had pushed everything too far, promising things that I didn't know I wanted but now those ideas were planted in my brain and taking root. Sure, I might have been able to take some of the medium sized dildos in there but those truly huge ones were almost parody, something to laugh at. Now? Jamie bent over, butt wet from lube and asking for what was hanging off my crotch, looking over his shoulder with excitement as I went to him...

Shivering, I closed my eyes and felt feather light touches of pleasure flow down and over my body, my breathing rapid and harsh by the time I came down. Shifting in my seat, aware I'd just had a mini-orgasm in the parking lot of a sex toy store, I kicked the car in reverse and started my slow way home. It took awhile but that was fine, giving me time to cool down as I sang along with familiar songs provided by the radio.

By the time I made it back, the sun had fallen and winter darkness laid claim to all. Parking carefully, I flipped on the dome light and tucked the brown paper bag into my backpack before leaving my car for the night. I walked into the dorm house and noticed the couch absent of Donna but with the shower running, that wasn't much of a mystery. Closing my bedroom door behind me, I slumped on the bed and sighed. While I needed a shower badly, I'd have to wait for the hot water heater to refill and, oh whatever was I going to do in the meantime?

Pulling out the butt stuff, I opened the strap on box and dumped it out on the bed. Two dildos, a strappy mockery of panties, and a page of instructions spilled out, inert yet potent; dead without a couple to fulfill it's purpose. Sure, the actual thing I'd be wearing didn't exactly look comfortable but all that mattered was that it worked. Picking up the smaller dildo, I observed what very well could be going into Jamie soon.

It was, of course, pink and smooth, not very wide or long. Compared to some of the monsters back at the store, this thing was cute and not at all threatening. The second, purple one was bigger, fully formed and close to Jamie's measurements by my rough estimations. There was no way I was going to lead off with this one. The pink one, which had to be named Big Clit, was so much more welcoming.

A knock at the door pulled me back, making me aware I was holding and fantasizing about a fake dick. Sweeping all my new toys under the blanket, I gave a tired 'yeah?' and Donna opened the door, asking if I was up for a burger run. I declined, citing homework and needing to shower, Donna leaving my door ajar as she walked away.

Taking a few deep breaths, I flopped on my back and hoped some day for a place of my own. Then I wouldn't have to frantically clean up after having fun with Jamie or worry about when someone else was here during out limited time together.

The front door being slammed shut broke that train of thought, getting me to my feet and to the living room as I heard Donna's car purr to life. Heading to the kitchen for a bottle of water, I lingered until she finally left, an idea forming in my head during that time.

With her gone, I finished off the water and returned to my room, making sure the door was shut behind me, just in case. Stripping my pants and underwear off, I tossed the blanket to the side, revealing my hidden horde. It took me a minute to puzzle out the straps but finally got them pulled up and adjusted, snug but not too tight. My butt was completely exposed, with the ring that held the phallus resting over where Jamie had pushed back into me nights ago.

Hands shaking, I snatched up the big purple dildo and fumbled about for too long but finally, it hung off my crotch. I felt the weight of it, watched it wobble as I took a few steps, eternally erect and ready for action. Reaching down, I ran a finger from the tip to the base, the false veins adding texture the whole way.

Grasping it, I gave my new dick a slow tug. A few more, testing to ensure it wasn't going anywhere, getting a feel for doing this familiar gesture on my own body. Reaching down, I slipped the strap that went between my legs aside and took care of one need while addressing another. This, going where Jamie had wanted attention, pulling his hips closer as this sank in ever deeper, hearing his cries, knowing he felt as I did, as a woman did, his breasts rising and falling as he begged for more, deeper, faster...

Clutching the dildo I'd been stroking all the while, my legs buckled and I fell to my knees, blinded by the annihilating fury of this fantasy that had potential to be. Fingers and inner thigh were drenched in liquid heat, the fake penis holding up to my abuse well as I knelt by my bed, shuddering in nigh unbearable pleasure as it lorded over me. Low moans that sounded pained to my ears rang out as I slowly rose to the surface, the well of passion that I'd fallen into finally letting me escape.

Rising to my feet on still unsteady legs, I polished off the water on my bedside table, shocking at how weak I felt and how vivid that little session had been. Not since I'd stolen my first kiss from Cass and then spent the next few days desperately hoping for more had an idea driven me this crazy. Still, this was for later and if I needed a shower before, now, it was essential.

Carefully removing the strap on, I put it and Big Clit back in their box, then replaced that in the bag and slid it under my bed. All this was done on autopilot as I really had nothing left aside from a lingering question of how Jamie would respond to this. Finding pajama pants, I stumbled my way to the bathroom and ran a hot shower, the countless drops dancing on my skin and the humid air a treat to cap off this crazy day. Only the water cooling forced me out and I went to bed satisfied, knowing the next time Jamie and I found time together, we were going to have one hell of a talk.