A Shopping "Trip" Pt. 01

It was Saturday in the summer, and I was in that rare place where Basketball ended, but Football hadn't started. So my honey-do list was pretty small, and I had gotten up early and finished it before 10 AM.

I sat at the kitchen table drinking coffee and looking at the standard guy stuff tools, cars, and golf clubs when Cassie came downstairs. By the way, she was dressed, I could tell she had plans to spend the day with a friend. This usually meant shopping and lunch. She was dressed to the nines. High heels, stockings, a short skirt (just long enough to not be too slutty), and a tight top that accentuated her boobs.

I poured her a cup of coffee and gave her a kiss. "Morning, babe. It looks like you've got your day planned out." I smiled.

"Yep, Bree and I need to catch up and have some girl time. We've both been so busy lately." She gave me a kiss and sat down at the table to finish her coffee and check-in social media. Bree was Cassie's best friend, and I must admit I wouldn't mind seeing her again. She was a fiery redhead with a plump ass and nice tits that she wasn't afraid to show off in revealing outfits. She also knew she was hot and exploited her gifts, teasing and taunting men to see how much of a reaction she could get. I admit she had gotten a strong response from me a couple of times, but nothing more than flirting.

As I sat there picturing Bree's ass hanging out a pair of short shorts and fantasizing about a three-way with her and Cassie, Cassie's phone chimed several times as texts poured in.

"Fuck!" She shouted and put her phone down on the table.

"What's up, babe?"

"Bree's husband is an asshole! He's so jealous of her that he's made plans for them today and she has to cancel." She sighed deeply. "Now I have no one to go shopping with."

"That's too bad, hun. I wish I could help you, but I got a pedicure on Thursday." I joked half sympathetically.

Cassie shot me a dirty look and then turned her head sideways like she tried to understand what I said. Then her lips formed a wicked little smile. "You know, babe," She said in a tone that was a sweet as raw honey. "You could come with me, and I would make it worth your while." She stood up, turned her back, and bent over flashing her ass at me. The thing she was wearing left nothing to the imagination, and my cock started to grow as I sat there drooling. Finally, she stood up, came to me, and rubbed me through my shorts. "What do you say, babe? Will you be my BFF for the day?"

Now, like most guys, I am not a fan of shopping with women. They like to spend the day wandering around a bunch looking at everything. Me, I want to get in and out. So my first answer was a solid no, but Cassie persisted.

"Oh, come on, babe, You can pick out a few new outfits or panties for me, and if you're a really good boy." She paused for effect and brought her face right up to mine. Then, looking intently in my eyes, "You can have your way with me, whatever you want." My cock jumped in her hands, and I knew I was finished.

"Okay, I said, but I'm not dressing up." I said firmly, "Oh and I'm not getting my nails done." I realized I had to set some boundaries just to be safe.

So we headed to the mall, wearing faded jeans and a titans jersey and her dolled up like it was ladies' night at the local pick-up joint. I have to admit I enjoyed it when she bent over and flashed her ass. That thong barely covered her pert little rosebud, and my cock took notice every time she bent over. She was definitely eye candy, and it was quite the ego boost seeing how men and women reacted to how beautiful and sexy she was.

The first stop was for shoes, and Cassie took every opportunity to flash her panties at me as she tried on stilettos high enough that she would need government clearance to wear them. The poor salesgirl was definitely overwhelmed by Cassie's teasing. She blushed when Cassie asked, "Do these make my ass look tasty?" and bent over, grabbing her ankles.

"Definitely" I smiled and licked my lips. I didn't know what Cassie was thinking, but the salesgirl was cute and curvy with huge boobs. I was up for a threesome. Alas, it was just a tease, and all she wanted was a new pair of heels. So we paid, and I said goodbye to the salesgirl and her boobs.

Our next stop was for makeup. Cassie spent an hour with a petite Asian woman creating different looks. Kai (the makeup artist) had small breasts; Her huge nipples poked out of her smock about an inch making it impossible not to notice them or wonder if they were that big because she was excited or if they got even bigger. I spent most of the time watching sports on my phone but was always interested when they finished a new look, and Cassie Modeled it for me; the highlight was when Kai spilled something on her smock and had to change it. She was wearing a tight, thin satin camisole and yoga pants underneath. Her body was fantastic, and I almost ripped the zipper out of my jeans. Her areola were silver dollar-sized, and her nipples pierced. The right one was a barbell, and it looked like the left was a hoop. The way the yoga pants hugged her petite frame was obscene. They left nothing to the imagination. From the overstated camel-toe that was begging for a stiff tongue. The way the back lifted her butt and separated her cheeks as if she held them open for my cock. She may have been petite, but she was incredibly hot, and from the piercings and the way she dressed, I would say pretty adventurous; I think she caught me staring ogling her, but she smiled, so I was home free. I was disappointed when she put on a clean smock and went back to selling makeup. If I had any say in a three-way, it would definitely be Kai,

Cassie made the most of the time getting a tutorial on a bunch of different styles. The looks ranged from sexy to slutty, and all in all, we spent $500 on new stuff. It's a bit extreme for me, but if it makes Cassie happy, then she makes me happy.

We hit a dress shop before lunch, and Cassie tried on several micro-mini dresses and skirts. She took every opportunity to flash me and everyone else in the shop. This caused a bit of a stir and a couple of heated exchanges between another couple when the guy got caught staring. His gal was disappointed with him and then got pissed when she noticed his hard-on. This was just fuel for Cassie's fire. She turned her back and bent over, giving them both a view that might land them in divorce court. I'm pretty sure the saleswomen were all enjoying the show too. I wondered which ones wanted to see more. I have to admit as much as I knew the attention was dangerous, I enjoyed it too.

Lunch was a quick bite at a Mexican restaurant in the mall. A couple of street tacos and Jumbo Margaritas later, and I was feeling no pain. As we left the restaurant, Cassie kissed my cheek, thanked me, and said that we were almost done. She cupped my balls and smiled wickedly, saying she had saved the best for last. I was pretty sure there wasn't a porn shop in the mall, so I had no idea what she was thinking, but she had my attention.

She led me past a bunch of empty storefronts to a shop in the far corner of the mall. It looked like the whole wing was being remodeled, except for the one store named Seductions. The windows were filled with male and female mannequins wearing different lingerie and costumes. Some were mildly suggestive but in a rated PG way. A huge rainbow-colored banner hung below the sign declaring a lingerie sale and buy two get one panty promotion. I walked in, grinning from ear to ear, understanding what the best was. As we entered, it was clear that Cassie had been here before. I recognized some of the lingerie from her collection, and the saleswomen knew her by name. I would like to say there was some amazing

babe working, but after the experience with Kai, they were just meh.

The front of the store was filled with a bunch of gag gifts and bachelorette party games, but as we went further in, things got a bit more risque. Sex books and a few vibrators filled the shelves, and the costumes and lingerie on the wall had a BDSM theme. There was an incredible selection of lingerie and panties, probably everything you could imagine.

The shop, which looked pretty small on the outside, was huge inside, and the deeper we went, the more depraved things got. I was both curious and nervous about what we would find ahead, but I followed Cassie obediently.

The mannequins were posed provocatively, including a couple of group sex displays with anatomically correct figures that left no one's preferences out. Cassie got behind one of the male mannequins and grabbed his hips, thrusting his cock in and out of the other mannequin. She gave me a wicked smile and then walked behind a couple of the racks of costumes out of sight.

I looked around at some of the costumes, a naughty nurse, a naughty maid, a naughty cop. I have to admit I liked the theme and couldn't help but think of Cassie role playing for me. Although, to be honest, I'm not that comfortable playing a part, and roleplay meant her dressing up and me undressing her.

I had just started looking at crotchless panties when Cassie came back. She was wearing a black satin cheerleader outfit with white thigh highs and stiletto heels.

"Oops, hold on," She said, turning around; she bent over to fix the strap on her shoe and gave me a fantastic view of her perfect ass. The white satin thong riding up between her cheeks contrasted perfectly against the skirt. I was mesmerized. Caught up in how sexy she looked and how hard my dick was. I stood there, mouth wide open, thinking about pulling down those panties and stuffing my dick in her tight little asshole.

Cassie, Looked back over her shoulder and smiled. She stood up slowly and turned to face me. Even if I wanted to, I couldn't hide my raging boner. She smiled and curtsied, and I got a quick glimpse of her panties, A pink accent caught my eye, but I couldn't tell if it was a word or lace. Finally, she came over and grabbed my hand. "Well," she said in a sweet whisper. "I don't think it's fair if you don't get something for being such a good girlfriend. Substitute girlfriend" She corrected herself quickly. She started browsing through the thong panties. I couldn't help but think this was a gift that I would enjoy taking off of her again and again. Cassie picked out several pairs and walked toward the back of the store. I stood watching her walk away and waiting for her to try them on and make her decisions.

Cassie stopped suddenly in her tracks, glancing over her shoulder. "Are you coming, babe?" She hiked up her skirt, exposing her beautiful butt. "Oh, I know how to get you to follow. Come on, baby, come here, my little anal slut." I really didn't need that much encouragement, but it worked. I almost knocked over a rack of robes. Cassie came and grabbed my hand. "Easy tiger, you'll get yours soon enough." She walked me slowly to the back of the store toward the dressing rooms.

There was a counter in front of the dressing rooms. I think it was where they would check the number of items you were trying on to thwart potential shoplifters. I looked around for an attendant, but there was no one about. Finally, Cassie put a finger to her lips as a signal not to make a sound and reached over the counter and grabbed a key. She winked at me and walked behind the counter, past the dressing rooms, and to the door off to the side. She used the key and let us in.

The room looked like a studio apartment. It must've been for emergencies when the manager had to stay over, and it looked like no one had visited recently. Everything was clean and in place, like a hotel room; on the far wall was a bed that had been turned down.

I looked at Cassie, puzzled; I really wasn't sure what was going on. Finally, she smiled and took off her top, setting her boobs free, swaying right in front of my face. She grabbed the back of my head and pressed my mouth to her nipple. At that moment, I forgot about everything and decided to just go with it. While I sucked her tit, she undid my pants and took them and my boxer briefs off. I felt something on my legs and tried to look, but she held my head firmly to her breast.

Something silky brushed my dick, and I felt something pressing into my ass crack. I pulled away and looked down to see she had put a silky pink thong on me. I grabbed at the waist to take them off, and she put her hands on mine. "Come on, baby," she cooed. "It's role play. Don't you want to have some fun with me?" She rubbed the silky thong against my cock, and my erection got in the way of my argument. There's a bit of irony that she massage my manhood with the panties she put on me.

Now as much as I had never thought of wearing panties, I have to admit that her rubbing my cock through them felt terrific. As I started leaking precum, she leaned into my ear and whispered, "well, I guess we have to buy these now." I began to tense up, feeling my cum starting to boil up, and she stopped suddenly. She spun me around and placed her hands on my butt. "Mmmm babe, I see why you like it when I wear thongs. Your ass looks so amazing." As she said this, she ran a finger down my crack and grazed my butthole.

I nearly jumped out of my skin, and she reached around and started stroking my cock. She took her finger away from my ass and then brought it back. This time it was slippery as she rubbed me. Caught up in the handjob, I didn't realize what was happening, and before I knew it, she pushed her finger into my ass. I started to pull away, but she dropped her hand to my balls and gave them a squeeze. I froze in pain, and she leaned into my ear again. "Don't fight me, baby, cause you can't win." Her tone was a mix of sweetness and strength, and I decided not to test her resolve.

She went back to stroking my cock and started to finger fuck me. After a couple of minutes, the sensation went from pain and intrusion to pleasure. My cock throbbed with every thrust of her finger. Cassie took notice of this immediately. "That's it, my little ass slut. Let yourself enjoy this." Her voice was back to sweet and sexy.

I was enjoying the fingering and stroking so much, it didn't register in my brain that she had called me her ass slut. When it did, I tried to determine what she meant. Was I an ass slut cause I like fucking her ass or because she was fingering mine? I heard someone moaning and then realized it was me. Embarrassed, I blushed and bit my lip to keep quiet. I think that's when she knew she had me completely in her control. I felt her hand on my back gently guide me forward, and then something warm and wet on my butthole, She grabbed my cock through the silky panties and started stroking, and just as I was starting to feel a climax build again, I felt pressure on my hole. She began stroking faster, and I felt something penetrate me. It was bigger than her finger and immediately uncomfortable. I groaned in pain as it stretched me open, and my hard-on disappeared. "Just relax, baby, just breathe and let your ass adjust to it." Her voice was soothing, and she continued stroking my cock, keeping it in that limbo state between fully erect and flaccid. It felt good, but the pain in my ass was distracting me. I took several deep breaths, and little by little, the pain subsided. After a couple more minutes, the feeling changed to that of feeling full, my body relaxed, and my erection returned better than ever. Cassie slowed her strokes down, not wanting me to finish, and pulled the beaded wand out of my ass. She began to slowly thrust it in and out of me. This time the sensations were incredible. So good that I wasn't aware of her hand on my cock. I was moaning again, louder, and I didn't care.

Cassie stopped everything. She grabbed my balls, squeezed, and pulled them away from my body to keep me from coming as she pulled the toy from my ass. It felt so good. My knees were wobbly.

She rubbed her boobs against my back and leaned into my ear. "Listen, baby, I promise I will make you feel good, and I won't do anything you don't ask me to, but" she paused to build anticipation, "but if you wanna be my slut. Well, you have to dress the part." She walked to a table and grabbed a shopping bag,

I got a bit nervous; I wasn't sure what she had in mind. I'm standing there in a pink thong. What's next? She reached into the bag and tossed it to me. Inside was a football jersey. I put it on and looked in the bag to see if there was more.

"That's it, babe." Cassie said, "So I wanna roleplay, but really role play. Not just dress up and fuck. Can you do that for me, babe?" Her tone was comforting and sexy, almost hypnotic. I nodded. She grinned from ear to ear. "Okay, here's the setup. You're the stud QB sure to be in the top five of the draft. I'm the slut cheerleader. I caught more passes than your favorite receiver. You're in the locker room after practice. You think you're alone, getting dressed after your shower. I walk in on you, and your panty secret is out." She looked me deep in the eyes. "Did you get all that?" I nodded. "Are you ready?" I nodded again. Cassie handed me my jeans and pointed me across the room. "Okay, go stand by the bed with you're back to me and act like you're getting dressed."

THE LOCKER ROOM ROLEPLAY

It had been a challenging practice, and I stayed late to get treatment. I decided to watch a film after that and was all alone in the locker room. Even the janitor had gone home. I took a shower and was getting dressed. I put on my jersey and reached into my duffel bag for some boxers, and found Jenna's (my girlfriend) thong. I snuck it away from her last time we hooked up. I held them up to my nose, breathing in her scent. Man, I love the smell of pussy. They felt so soft and silky in my hands, and I wondered how they would feel. I looked around the locker room to make sure I was alone and slowly slipped them on. They were tight but stretched to fit me barely. The silky fabric felt so good against my cock, almost enough to take my mind off the strip riding up my ass. It was both uncomfortable and pleasant. It was a strange sensation having the thong rub against my butthole, not bad, just different. My cock grew in the panties poking way out of the top f the waistband. I was lost in the sensation and taboo moment when I heard a wolf whistle behind me and froze.

Cassie Allen was the biggest slut on campus. The head cheerleader had her sights on Alex for a while, but he had always refused her advances. Finally, she made a play at his fraternity Halloween party, he was really drunk, and Jenna had gone home early to study, but no luck.

She wanted him, no needed him. He was her white whale, the big one. No man had been able to resist her, no man except Alex. She had been planning and plotting and knew his routine by heart. She knew he would stay after practice on Monday to prep for the game week, and today was the day. She was going to surprise him in the locker room and make him an offer he couldn't refuse. She dressed up in a super tight satin black cheerleader outfit she found online. The top was tight enough it barely contained her 38 DD boobs, but sheer enough, you could see all of her nipples poking out. The puffy areolas were the size of a silver dollar, and her stiff nipples were pierced with barbells. The skirt was so short it didn't cover her ass. The hem fell about halfway across her cheeks, leaving nothing to the imagination. Contrasting the black outfit was a white thong and thigh-high stockings. She finished the look with platform stiletto heels. She was dressed to seduce. She talked the janitor into letting her in the practice facility, saying she had forgotten her backpack and needed her laptop for class. Once in, she was in, she made her way to the locker room and her prey.

There wasn't much that could shock her, but she was more than a little surprised by what she saw. The stud football player wearing a jersey and pink thong panties. She grabbed her phone out of her oversized purse, snapped a couple of pics, and then whistled at him.