Caught Out Again and Again Ch. 6

I related to Cheryl my girlfriend about the grocery shopping episode. It was two college bullies from the women's rugby team that had trapped me in an aisle at the back of the store. They caught sight of my panties peeking out as I had bent over to pick up something from a lower shelf. They thought I was a girl until they spun me around and took a close look at my face; even then they weren't quite sure.

Both of them were bigger and taller than I was and blocked any path to escape. Then one of them grabbed my crotch and confirmed I wasn't a female. Even being that scared, being exposed in public by two strange females was exciting and a boner grew between my legs.

Cheryl laughed at the tale as she had me bent over. I grabbed my ankles as she fucked my ass with her large strap-on. I guess I was overly excited and came inside my panties.

She unsnapped her harness and left me there; bent over with her cock still deep inside me. She walked to the bedroom. "Come on. Let's change. I want to go shopping!"

I followed her on wobbly legs. She had her outfit laid out on the bed: a luscious, red coloured wrap dress. She removed her kimono robe. She was already dressed in a white bra and thong with garters and stockings. "Your stuff is in your change room. And fix your make-up! "

I decided to clean up a bit before I went to my change room which was actually my home office. I looked in the mirror and saw my face was a smeared mess. I re-applied some blush and shade, brushed on some heavier mascara and used a bright pink, sparkly gloss on my pouty lips.

I stripped off my grocery shopping clothes and lingerie. I recognized the Secrets in Lace bra Cheryl selected for me. It was a black, full cup, balcony bra from their Sheer Seduction line. I reached back around and hooked the eyelets before slipping the straps over my shoulder and adjusting my fake boobs. The cups were sheer so the big, hard nipples poked through.

The panties weren't really panties. It was a teeny G-string. The triangle crotch was so small, it barely cradled my balls and left my cock overflowing the top. The stretched, back string dug hard between my bum and into my asshole. My dick was already getting semi-firm.

The six strap garter belt was also from the S-I-L Sheer Seduction. It rode high on my hips and when attached to the lacy welt, would stop my fishnet stockings from falling down.

Hanging on the door was a blouse and a black leather skirt. I put on the blouse. The white was opaque enough but my bra would easily showed through. With the top three buttons undone, my bra would peep from the gaping vee front anyways. I zipped up the back of the soft kid leather skirt. From my waist, it was barely twelve inches long and quite tight around. And while the hem just covered my stocking welts, my garter clips and my semi-erection made slight bumps in the otherwise smooth, flat skin. Bending over would make it impossible to hide my garter straps especially with the high slit running up the back. It ended barely an inch below my bum.

I thought that since we'd be walking around, I'd wear my pair of open toed pumps with only three inch Cuban heel. My bright pink painted toes wiggled through my stocking mesh.

"Well, don't you look pretty?" I heard from the doorway. "Give us a spin!"

I smiled and twirled around a couple of times. The skirt crept up as I turned. Embarrassed, I pulled the hem down as Cheryl let out a loud wolf whistle. "Are you wearing panties?"

I turned to her and sheepishly lifted the hem over my thighs showing my micro G-string and my stiff cock sticking out.

"Very nice." She smiled. "I think you need some accoutrements. Come."

From her jewelry stash, Cheryl handed me an eighteen inch string of perfect grey matched pearls and had me clip on some matching, dangling, pierced pearl earrings (difficult with my lengthy painted nails). She penciled in a darker, thicker eyeliner and framed my lips with a three shade darker lip liner. She stood back and gave me an approving nod. My eyes teared as I looked in the mirror and saw a very pretty hot girl looking back at me. "Don't ruin your mascara!"

The two of us made our way to the elevator. I was no longer concerned about my changed appearance that was until the doors opened to an older couple somewhere from the upper floors. The old letch eyed me while "granny" shot darts from her eyes to both me and her man. When they exited the car at the main floor, I watched granny slap at the old man, scolding him. "What were you looking at?"

The doors slid shut and descended down to the garage. Cheryl said she'd drive which was fine since I could relax in the reclined passenger seat.

I opened the door and placed my bum into the seat. The short leather rode up and exposed most of my stocking welts. I found it difficult to swing my legs in together without flashing anything. And then the back of my skirt split apart and barely covered my bum leaving half of my butt naked against the cool leather seat. Leaning back into the bucket seat caused my hem to shorten even more.

Cheryl drove like a maniac. She raced out of the underground and raced around the drive to the main street until she hit the first light. Beside us on the passenger side was a huge cement truck. From the corner of my eye, I could see the driver look down at me. I knew he could see my stocking tops and garter clips exposed due to my shrinking hem. Rather than trying to hide them and pulling my skirt down, I wiggled some so the hem actually rode higher until I could show him my naked thighs.

I wanted see how much more I was willing to show him but the light turned green and Cheryl stomped on the gas. "You're turning into a real slut aren't you Barbie?"

I giggled back at her as I pulled down my skirt.

The rest of the drive was a lot less exciting. Too bad all the vehicles that stopped beside us were about the same height as our car and so the drivers could not peek in. Cheryl turned into the mall outdoor parking lot. Rather than finding a spot nearer the entrance, she parked our car in an open area in the middle of the lot. As carefully as I could, I got out of the car and tried not to give anyone a free show. Fail! It would be about a 100 meter walk to the mall door.

As we strode across, I noted how Cheryl's leg would force its way out through the slit of her red wrap dress. Every once in a while, enough was exposed to show her front stocking clip. My flaccid cock stirred. It was then I realized that it had slipped down and out the side of my crotch piece. I wanted to fix it but Cheryl told me. "No. Leave it!"

We were about halfway from our car to the majority of the others. Cheryl "accidently" dropped her keys. "Be a dear and pick that up for me."

I knew it wasn't an ask. I looked down at the keys and wondered how to pick them up without being on display. If I bend over at the waist to pick them up, the back of the dress would ride up and my backside would show. If I knelt, the front would creep up and my stocking tops would peek out. I debated the lesser of two evils and opted for kneeling. But as I started to bend my knees, Cheryl stopped me. "Uh-uh! Feet and knees apart. Shoulder width."

A car had now stopped in front of us. I spread my feet and squatted as directed. My taut, back garter straps dug into my ass. Even with my relatively low heels on, I couldn't do it quickly without losing my balance or, maybe I just didn't want to do it quickly. I descended all the way down until my bum hit my heels knowing the male driver could see up my dress and perhaps my boy thing. I grabbed the keys and quickly stood.

"Thank you, Barbie!" Cheryl smiled. "I'm sure that gentleman thanks you too!"

As we passed the car, the guy turned to me and winked. His female partner was busy on her phone and didn't even notice. Pretending to be way above his league I ignored him but inside I was screaming with joy at the fact he thought I was hot!

In the mall, as Cheryl and I strode around, I noticed how many of the men ogled us overtly while many of the women sneered at us in distain. The more they sneered, the more I wiggled my bum until I felt something let go. One of the clips holding my stockings popped and I guess I showed some concern on my face.

Cheryl noticed and asked. "Barbie, what's wrong?"

"I need to go to the men's." I whispered in response. I panicked and had forgot how I was dress at that instant. "My garter snapped and I need to fix it."

"Well?" Cheryl looked at me. "Fix it! We're too far from the WOMEN's room."

"Here?" I dared question her knowing there was a bathroom just around the corner. "In the middle of the mall?"

Her answer was a steely stare. She crossed her arms under her boobs and balanced herself on one foot while impatiently tapping the other. I looked around and saw dozens of busy shoppers milling about. Given little choice, I bent over slightly and pulled up my hem enough to expose the undone front clip. My hand shook so much that redoing it took much longer than it should have. Clip re-secured, I stood back up and saw a number of males gawking at me. Then Cheryl insisted I check the others to make sure they wouldn't snap. So I pulled my entire hem up and checked each of the five other clips in turn. I looked around at the guys again and many had their hands in front of their crotch I guess to hide their boners.

All checked, I stood up and couldn't find Cheryl. She had left me undefended out in the open. I began to panic when I heard. "Barbie!"

I looked towards the voice and saw Cheryl in a store waving me over. I double checked my dress and waltzed over making sure every guy watching would see me wiggle my ass at them.

Cheryl was inside and beside a purse display. "I think this would be nice to go with many of the outfits you have. And even with what you have on now. But you'll need something when we go for dinner tonight."

I looked at the beautiful, red leather, Coco Chanel clutch. I really didn't catch on to her last comment. I gasped at the price tag. "It's beautiful alright but I can't afford to buy something like this!"

"Yes, you are right." Cheryl smiled. "So I'll buy it for you. A gift in a way. I'm sure you'll figure some way to appropriately thank me. And now, you'll need some shoes to go with."

After Cheryl purchased the purse for me, we walked around trying to find the perfect place to buy shoes. Cheryl stopped suddenly and declared. "Here!"

The store was in the back and out of the way from the main mall. The store was pretty intimate and lacked customers but displayed a fairly large number of shoes. As we entered, we were greeted by the lone but easy on the eyes salesman.

"Good day, ladies." Said he while eyeing me. "I am Greg. Please feel free to browse. We have a great selection. And if you have questions or would like to try anything, please just ask."

Greg's average sized body looked good in his dark, well cut suit. He had dark hair and was slightly taller than I was in my heels. As Cheryl and I looked around and picked a couple to try, I couldn't help but sneak peeks at him. Cheryl of course noticed. "He is cute. Not my type though; could be yours."

I handed him the samples and asked if I could try them on. Although I gave him my shoe size, he insisted on verifying it on that size doohickey measurement thing. He helped my remove my shoes and gently guided each foot into the metal device. "If I may be so bold, you have beautiful feet."

I felt myself blush as I looked down into his lobo grey eyes.

Cheryl continued to browse while I sat and waited in the arm chair he directed me to. Greg returned with a number of boxes and sat on that shoe store stool with the slanted foot rest. He cradled my calf. "May I?"

Greg raised my foot and slipped on the black, closed, pointy toed pump. The heel was only four inches high. He placed my shod foot on the floor and raised the other. Rather than keeping my knees together, I let my legs relax. He smiled. I knew he could look up my skirt, but how high up could he see.

He placed the other shoe on my foot and asked me to walk around. Cheryl looked and immediately said. "No!"

I sat back down but noticed how much closer Greg brought his stool. It was right between my feet and I couldn't help but keep my legs parted. Now I knew he could see my dangling doodle.

He took off my left shoe and placed my foot high on the sloped foot rest. With him sitting so forward, my toes were millimeters from his crotch. I wiggled my mesh stocking toes as he removed my other shoe. He minutely shifted forward. I felt him unembarrassedly grow as I brushed against his cock. He gave Cheryl a quick peek before bringing my right foot up to rub against his face. He gave my toes a suck, then a quick kiss before slipping on the shoe.

We tried a number of others shoes. Whether I had shoes on or not, he now placed my foot firmly into his balls. With shoes on, I made sure the heels were pressed in under his balls. In fact, I felt my shoe heel pop through the seam of his pants as he shoved his ass forward.

Even though I wasn't too crazy about them, he convinced me to try on some thigh high boots; bright red with thin, five inch heels. The tops were nearly crotch high. When Greg helped my pull them up, he slipped a hand under my skirt and gently caressed my now erect cock. "Nice, but not really sure I like these... The boot I mean."

"Try these!" Cheryl handed Greg the sample. He scurried off to get my size. "He likes you. See what kind of deal you can make."

Greg returned with a box in hand. I still had the thigh high boots on and there basically was only one way to get them off. With his back towards me and my foot between his legs, Greg grabbed the boot heel. I'm not sure how much he was trying since he wasn't tugging that much but he was humping my foot!

He bent over slightly and I could see the hole I made in the ass of his pants. I placed my other foot on his butt pushing my heel through the rip. As he continued his pretend effort, I pretended to push with my foot but instead pushed my heel into his crack. Alas the boot finally slipped off. The other boot was still fun but less eventful.

Greg sat on his stool in front of me; my foot firmly pressed against his erection. He uncovered the box and the paper but when he unwrapped one of the shoes from the protective bag, I gasped at the beauty. The open toed shoe was red with sparkles a la Wizard-of-Oz Dorothy. It had a half inch platform and a pointy, six inch, slender steel, stiletto heel.

Greg gently slipped the shoes on my feet. They fit perfectly. I stood up. They felt perfect. With the heels on, I was now a couple of inches taller than Greg. As I took a couple of steps, Cheryl gave me a looking reminder. As coyly as I could, I wiggled my hips as I walk towards the backroom door way. With hands on hips, I turned my head over my shoulder and fixed a gaze at Greg before ducking into the back. Greg followed promptly.

Now hidden away from the open, Greg surrounded me with his arms. His firm hug was true and warm. His kiss was soft and sincere. He dropped to his knees. His hands slide down to my legs then up under my skirt pushing my hem northward until my hard cock was fully exposed. He gave it a kiss and then took me into his warm mouth.

His hands guided me forward until his lips finally reaching my base. He held me there, trying to take more of me inside but that was all I had. The tip of my knob brushed the back of his throat with each hump of my hips. I moaned out. "Oh fuck, baby!! You're going to make me cum!"

Greg slow pulled away and let my cock pop out from his mouth. He looked up and gave me a pouty smile. "Cum in me?"

With that, Greg rose from his knees. He undid his pants and let them drop to his ankles. Bracing himself against a chair, he spread his feet as wide as he could and offered his ass to me. His would be my first... male that is.

With my heels on, I was at the perfect level. I pointed my dick into his crack and slowly pushed forward with constant pressure waiting for some sort of resistance. I met with none. I felt the head of my dick slowly enter him. He was tight but I popped though without issues; the rest of me slid right in.

"Oh gawd! Fuck yeah!" Greg cried out. "You feel perfect!"

As I pushed forward, Greg pushed back. Slowly at first but soon our pace picked up until I was slamming my hips into his ass. "Fuck! Fuck! Fuck! Fuck!"

"Oh, Greg baby! I'm going to cum in your ass!" I moaned out.

"Yes! Oh fuck! Uh! Yes, cum!" Greg begged. "Cum in me! Uh...Uh...! Cum in my ass! Now!"

I couldn't hold back any longer if I tried and dumped my load into his naked asshole. "Oh! Oh! Ooooh...! Fu...c...k...!"

I collapsed atop of Greg. My spent dick quickly wilted and was spat from his ass. I fell back into a chair panting. My cream dripped from Greg and down his legs.

He turned to me. His eight inch cock was rock hard and was dripping pre-cum. He moved towards me. Moving between my legs, I thought his was going to clean me off but instead he lifted my spread knees with his hands. In my mind I started to panic knowing what was coming next but with all my strength sapped, I couldn't protest.

Greg pulled my thong string aside and pushed his thick cock inside of my ass. My lack of resistance made his entry easy as he pushed pass my protective outer ring. I just closed my eyes and enjoyed his wondrous wood deep inside of me. I let up a guttural "Aaahhh...!" as he slowly pumped me. My own cock came back to life. It flopped up and down with each of his determined thrusts. My pre-cum poured out onto my belly.

Greg's shaft found and nudged my prostate. I knew I was about to cum again. Then there was a sense of hot wetness in my bowels. I began to spasm as more cum spurted onto me and covered my skirt and blouse.

As he extracted himself, I felt my hole close and sealed his seed inside of me. He gave me his contact number. I gave him mine. I cleaned him off before I walked out with my new shoes.

I wanted to see him again.