Brittany's First Time Out

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven skin. I topped the look off with my curly blonde bombshell wig. I'd never been an expert with makeup, but I was proud of the passable job I'd done despite my nerves.

"I shouldn't be this nervous," I remarked to myself. Even though I'd looked forward to this night all week, the reality was rather mundane. All I was doing was going for an evening drive. During that time of night, there'd be scarcely anyone on the roads and even if there were someone there, they wouldn't see me. I wouldn't even be getting out of the car. Nothing could go wrong. Despite my reassurance, though, I couldn't calm my nerves. It would be the first time I'd left my house while dressed up.

I shuffled into my bedroom and considered my outfit for the evening. I began by securing my cock into my pink silicone chastity cage. Once I was snugly locked, I covered up the cage with a white frilly thong. My reflection in the mirror caught my eye. Even with the added bulk the cage adds to my cock, it's small enough to get lost in the frills of my panties. Any scrap of manhood that was there to begin with was next to invisible. I let out a girlish sigh as I ran my hand over my feminine crotch.

My stockings were next. The white silky material flowed over my legs with ease and rested just below my soft, round butt adorning my thighs with the lace tops. I couldn't help but lie on my bed and revel in the feeling of rubbing my satin covered legs together. My cock was already beginning to swell in its cage. I felt my nerves beginning to calm.

I stepped over to my dresser to retrieve a white lace bra that matched my thong. Once I'd slid the straps over my shoulders, I slipped in some D-cup silicone breast forms. With my girlish figure complete, I couldn't pass up an opportunity to pose. I stood in front of my mirror and watched as the girl looking back at me danced around, blew kisses and showed off her cleavage and cute ass. I was having a bit too much fun.

It was time to finish off my outfit with my favorite dress and my fluffiest white petticoat. I pulled the dress out from the closet. It was soft pink satin with white lace trim, puff ball sleeves, and a peter pan collar. The skirt came down to the middle of my thighs but after I slid the petticoat up my legs and into place, you could almost see my stocking tops. To complete the dress, I tied on its white frilly pinafore with a big bow that sat above my waist.

All I had to do then was slip on my shoes and stroll out the door. I slid my feet into my pink platform stilettos with 6-inch heels and stood up to grab my purse. As I packed my cell phone, wallet, and car keys into my clutch purse, an idea occurred to me that would make this outing more interesting. I teetered on my heels a bit but made my way back into my bedroom. I dug through the drawers beneath my bed until I found what I was searching for: a bulbous, black buttplug with a curved base.

I grabbed some lube from the same drawer and lubed up the silicone toy as I pulled down my thong. This was one of my larger toys, so I had to take care when inserting it. I lay down on my bed and lubed my asshole liberally; then began to tease myself with the tip of the plug. A moan escaped my lips as I pressed the toy into my eager hole. My cock strained against its silicone prison. The toy penetrated further into me as my breath caught in my throat. As I stretched to take in the plug's widest point, I bit down hard on my bottom lip. In that moment, I let out a long, girlish moan as my asshole passed the thick bulb and engulfed the rest of the plug. My head fell back in sissy bliss.

I lay across my bed with my ass completely full until I glanced over at the clock on the wall. It was already past three-thirty. I bolted upright on my bed. I hadn't thought about how long I wanted to be out but if I didn't hurry, I would lose the cover of darkness. I stood up and retrieved my panties from the floor. I slid them back up my legs and over the buttplug's curved base that sat flush with my ass. I stashed the tube of lube I was holding into my purse and after a quick makeup and hair check in the mirror, I headed for the door. As soon as I reached for the doorknob however, I froze. All my worry and fear returned in an instant as I was mere seconds from being exposed to the outside world. "I can do this," I tell myself. With a deep breath and every muscle in my body tensed, I opened the door.

My senses were overwhelmed after just a few steps off my front porch. The cool, autumn air against my stocking covered legs was like nothing I'd ever felt before. The breeze was trying its best to blow my curly blonde hair into a tangled mess and the clicking of my stilettos on the pavement was deafening. I opened the door to my grey civic and closed myself inside, my heart racing. I was exhilarated and terrified at the same time. Every miniscule thing was a shock to the senses from how my manicured fingers gripped the steering wheel to how my dress rode up in the back exposing my pantied ass to the leather seats. It took some time for me to calm down, but after the fear began to melt away, my excitement helped me press on. I couldn't help but smirk seeing my shiny red fingernail press the engine start button.

Driving with heels, I found to be exactly as difficult as it sounded. After some practice and seat adjustment, however, I found myself getting along well enough. I'd even calmed down enough to throw together a music playlist. I cruised down the road, belting along to Taylor Swift and Ariana Grande. I was having the time of my life.

Along a particularly quiet road, I'd passed a church that stuck in my mind. The parking lot was partially hidden from the road, and was rather well lit. The lot was totally empty, and no one lived near enough to peek out their window at it. When the idea entered my head, I couldn't shake it. "What if I were to park there and take a walk around? It's a church so it's not like anyone will be there at this time of night." Just the thought caused pressure in my chastity cage. This was far riskier than I'd planned on being tonight, but the combination of my own excitement and the amount of girl power songs I'd been singing along to had me pulling into the parking lot before I knew it.

For some time, I sat, frozen in my seat, unable to make any progress toward the door handle. I could only stare out at the church's campus. It was rather nice. There were multiple buildings sprawled across a well-groomed lawn. There was even a playground.

After staring out my windshield for what felt like hours, I finally unbuckled my seatbelt and stepped out of the car. I began walking toward the side of one of the buildings. I hadn't any plan or sense of direction. I simply wandered from building to building listening to the rustle of my petticoat and the clicking of my heels. Each step I took I felt the plug in my ass shift about. I turned the corner away from the parking lot, towards more buildings and the playground. This area was hidden from the road and many of the street lights, so I felt safer. I strutted down the path, practicing my model walk.

I found myself at the small playground, considering the swing set. My inner child took over and I raced over to the nearest swing. I sat down and thought to myself how this would be my first time swinging in a dress. I make-believed I was a girl on a school playground and made sure to swing with my legs together as to not show off my panties to the boys. I giggled to myself. I slowed my swing to a stop, stood up, and straightened my dress. I supposed it was time to head back to my car. I'd taken enough risk for the evening.

I strolled back in the direction of the parking lot, but when I turned the corner my heart sunk to the ground and I stopped dead in my tracks. Parked in front of my car was a blue and white police cruiser. Stepping out of the cruiser was an officer who began shining a light into my car. I began to panic. I had to do something before he looked over and saw me. I ran back to the edge of the building to hide but my heels were like firecrackers the entire way. The officer's head whipped over, and I heard a stern deep voice yell, "Hey! I see you behind there! Get over here!"

I was caught. I leaned my back against the building, defeated. There's no way I could outrun him in these heels. Even if I did, he's still got my car. I had no choice. I slowly stepped out from the shadows and shakily approached the officer. As I emerged from the side of the building, his brow furrowed, and his mouth stood agape. He was as speechless as I was.

The closer I got to him, the more I realized just how tall he was. Even in my heels, he stood inches taller than me. My eyes went from his shoes, up his toned body to his sculpted jaw and piercing eyes. I stared for a moment then looked away.

"Ma'am, would you...care to tell me...what you're doing out here?" he asked. I couldn't help but blush at him calling me "Ma'am." I tried to put on my best girl voice.

"I-erm-I'm just...uh..." He stared at me intently, his eyes traveling across my body. "J-Jus-Just...taking a walk." I stumbled out, finally. He was silent for a moment.

"Taking a walk...at four-thirty in the morning...on private property?" he asked, bemused.

"Um..." A single sound was all that could escape my lips.

"Ma'am, can I see some ID?" he asked in a firm tone. ID? My mind flashed to driver's license hidden in my purse. There's no way I can show him that.

"I...um...don't have it on me," I lied, trying to sound as breathy and feminine as possible. The officer narrowed his eyes.

"What's your name, ma'am?" He demanded.

"B-Brittany." I answered, giving him my fake girl name. His expression didn't change, as if he were waiting for me to finish my answer. "Stone." I finished, realizing he wanted my last name too. He took a deep breath.

"Miss Stone, there's been a string of robberies committed just a couple of blocks over, and unfortunately we've got no description of the suspect. We've been canvassing the area for suspicious persons. I'm afraid I'm going to need to search you." He explained. "Would you come with me please?" He asked, while taking my arm and leading me over to his car.

My eyes went wide. I was beside myself. "How could this be happening? Just a few minutes ago, I was on a swing having the best night of my life!" My thoughts raced as I stumbled to keep up with the officer.

"Place your hands on the hood, please" he instructed when we arrived at the car.

"Why did I have to be so risky? Why couldn't I have just driven around, singing Taylor Swift songs like I planned? Wh... "My racing thoughts ceased abruptly when the officer began running his hands over my body. His firm hands traced my back and shoulders and made their way down my stomach. I began to breath more heavily. He pressed his body against my back and cupped my fake breasts, searching every inch for anything hidden. His vanilla scented cologne filled my nose.

He knelt and focused his attention to my legs. The sheer size of his hands as they wrapped around my left ankle made me feel so small and feminine. He made his way up my leg and my breath hitched as his hands slid across my stockings, and firmly gripped my thigh. By the time he'd finished repeating this on my right leg, I'd begun holding my breath and had a death grip on the police cruiser.

His hands migrated towards my crotch, and before I could react, his deft hands had discovered my chastity cage. He tugged on it a bit and moved it about in his hands while I was doing everything in my power to stifle my moans. Finally, his hands moved away from my caged cock as he began probing other sensitive areas. A squeak slipped out as I felt a finger run through my ass crack, slightly agitating the buttplug.

"What's this?" He demanded, as he grabbed hold of the plug's base. At this point, my sheer terror, humiliation, and shameful arousal had rendered me next to incapable of human speech.

"Ahhhuuhh...I'm not sure..." I dizzily replied. The officer didn't seem to like that answer and began to slowly pull the buttplug from my asshole as I involuntarily let out another girlish moan. The plug emerged from my ass and the officer studied it intently. After that, he looked over and studied me intently. His expression seemed to have changed. He placed the plug onto the hood of his car and addressed me.

"Miss Stone, I'm afraid my next course of action here is to bring you back to the station for questioning." He explained. My body went weak and I leaned against the car's hood.

"But! I- "I began before he cut me off.

"However...given the circumstances, I think we may be able to make other arrangements." He explained in a smooth deep voice. I was relieved at this, but...what did he mean? He took a step towards me, staring deeply into my eyes.

"I've got something I need...taken care of. If you wouldn't mind helping me out, I may not mind pretending I didn't see you out here." He proposed while slowly removing his jacket and button-up shirt revealing his thick muscular arms and rippling abs covered only by a tight white t-shirt.

"Sure" I answered with an unsure tone. "What did you need help with?" I asked as my eyes traced his ripped chest down across his abs. His intense gaze moved from my eyes downward. He took my hand into his and guided it over to his crotch.

"This is what I need taken care of." Beneath the fabric of his pants, I could feel the shaft of his rock-hard erection. I ran my hand up and down his massive length. My eyes were locked upon his bulge. "Think you're up to the task, Brittany?" he asked, emphasizing my girl name.

I was rendered speechless yet again. "I can't do this. I've never even been this close to a man's cock before, nor have I wanted to. There's no way I can go through with this. This is disgusting. I'm not gay." My thoughts repeated as neither my gaze nor my hand had left the huge bulge in front of me. The officer chuckled.

"I'll take that as a yes." He confirmed and began to unbuckle his belt and unzip his pants. He took hold of me and pushed me downward until I was kneeling in front of him, his bulge now directly at eye level. "Time to put those pretty red lips to work!" He exclaimed.

I looked up at his waiting expression, and back down at the unzipped pants. I supposed this was at least a bit preferable than being paraded through a police station in my current state. I slowly tugged at the waistbands of his pants and boxers revealing inch by inch, the giant specimen before me. Finally, his pants released the tip and his cock sprung forth into my shocked face. He was easily 9 inches of thick hard meat. He didn't need to say another word. A feeling alien to me took over. The musky smell of his cock drew me forward. I wrapped my manicured fingers around his thick shaft, and I started stroking his dick. My glossy red lips found the tip and I took it gently into my mouth. I began to bob my head up and down while gently suckling on the tip of his cock. I looked up at him to find him clearly enjoying himself, his eyes closed, and head lazily tilted to the side.

I let my lips slip off his cock head with a satisfying "pop" sound and I began to gently run my tongue along the underside of his shaft. My stomach was turning at how disgusted I was to be sucking a man's cock but at the same time my own cock had swelled so much, its cage could barely contain it. Being at the mercy of such a massive dick while being dressed like a sissy princess made me feel more submissive and girly than I ever imagined I could. It was intoxicating. Each time his cock touched my lips, I could feel more of my inhibitions and common sense melting away. I needed more.

I slid my lips deeper and deeper onto his shaft, my pace increasing. Each stroke, I would go just a bit deeper until I started gagging on his smooth cock head. My mouth was trying its hardest to reject this intruder, but I persevered. I needed this cock in my throat. He seemed to notice my newfound determination.

"You like this cock, don't you?" He growled. I nodded my head quickly while gagging once more. He took my head in his hands, pulled his cock out of my mouth and angled me up to look him in the eye. "Tell me how much you love it." He demanded.

"I need your cock! Please! I need more! I love it so much!" I pleaded, out of breath and desperate. He smiled.

"Let me give you a little help then." He said as he turned my face back down to look at the throbbing member. Keeping a firm hold on my head, he began to vigorously face-fuck me. Tears streamed down my face as I gagged on his hard cock over and over again. I felt him probe deeper and deeper down my throat until my lips grazed the base of his shaft and my tongue brushed his ball sack. He throat-fucked me balls deep until I was dizzy and began to forget my own name.

He finally slid his still rock-hard wet cock from my mouth. When I was empty, I could only stare up at him with my mouth agape and my tongue hanging out, panting to catch my breath. He bent down and took hold of me underneath my arms. He lifted me up with seemingly no effort and placed me on my feet.

"Bend over the hood" He ordered. I hesitated, knowing exactly what he planned to do next. "Was I about to let this happen? Was I okay with letting someone fuck me in the ass?" I wondered. Being throat-fucked was certainly an experience and I had to admit in my dizzy intoxicated state, I was curious about what his massive cock would do to my ass. I obliged his demand and bent over the police cruiser.

He folded the numerous layers of my petticoat upward revealing my frilly thong. He slipped his fingers under the fabric and slowly pulled it down exposing my sissy asshole to the cool night air. I could feel his finger teasing my opening as he knelt to be eye level with my ass. He leaned forward and began tonguing my asshole, lubricating it with his saliva.

I let out a moan from deep within my soul as I felt his tongue penetrate my most sensitive opening. My entire body tensed up and my breathing became ragged as he probed every inch of my anus that his tongue could reach. As my asshole became more and more slippery, I remembered something I'd brought with me by accident, figuring I'd put it away when I got back. Through labored breaths, I managed to address the officer.

"I-I've got...some lube...in my purse...if you wanna use that" I suggested. He stood up and smiled.

"You sure came prepared, didn't you?" he teased as he turned and headed to my car, giving my ass a firm smack as he did so. As he went to retrieve my lube, I bit my lip and stared at his bouncing cock glistening with my saliva and lip gloss in the glow of the street light. I couldn't believe the journey I'd taken in the past two hours. I'd gone from a straight sissy who just wanted a night out, to getting turned on by a strange man groping me, to now. Here I was staring at a fat wet cock like it's a big juicy steak. I knew I'd never be quite the same again.

I didn't realize how long he'd been digging through my passenger seat until I snapped out of my own haze. He finally emerged with the small bottle and began to saunter back to me. I began to ask him what took so long, but the sight of his bouncing dick lulled me back into a hypnotized state. He popped open the bottle and soaked his cock in lube, massaging it in as he went. I drooled at the site of this.

"Back on the hood" he ordered. I obeyed immediately, positioning myself back over the car's hood with my ass sticking out ready to be fucked. He coated his finger in lube and slipped it deep into my ass still wet from his saliva. His finger coated everything it could reach in slippery gel then popped back out.