Sissy Kristy Gets Her Cherry Popped

Warning: this story depicts forced/nonconsensual sexual fantasy. If that's not your thing, then please move along.

It was about 11 o'clock in the evening and the Cash Saver parking lot was completely empty save for one car. I sat there in my car patiently waiting for my new friend. You see, I learned a few months back that I loved to suck cock and eat cum. I mean, I always knew that I would love it, but last month I finally got the chance to try, and it was amazing! Since then, I had sucked so many cocks I couldn't even keep up with how many there had been. Now, I was waiting to meet this guy Rick that I had found through a craigslist ad.

According to the ad he posted, Rick was actually wanting to fuck some sissy ass. I still hadn't tried anal with an actual guy yet. Sure, I used dildos and toyed my ass often, but I was just not ready to be butt fucked. Especially not by a complete stranger. But I liked the pics Rick included in the ad. He was an older dominant guy with a really nice cock so, even though I wasn't really what he was looking for, I messaged him anyway.

Lucky for me, he hadn't had any luck finding a sissy willing to give him some ass so he agreed to let me suck him off instead. The only problem was that I didn't like to host strangers at my place and Rick couldn't host at his place because he was married. Thankfully, Rick said he knew of a place where we could have some privacy. The plan was for us to meet here in the empty lot. I would then get into Rick's car and Rick would drive us to a secluded place that was close by and I would swallow his load. It all sounded yummy to me!

As I waited, I pulled down the vanity mirror and checked my makeup once again, reapplying some lipstick. I thought I looked absolutely gorgeous. I was wearing a short blonde wig, and glasses that perfectly framed my cute face. I also had on a black lacy tank top, tight daisy dukes that showed off my little round ass and some red converse that accentuated my smooth toned legs.

When I folded the mirror back up, I noticed some headlights coming towards me in the parking lot. The car pulled right up alongside mine and I could tell it was him. Finally! I grabbed my little purse, got out of my car, and locked the door. Then, I opened his passenger side door and my jaw dropped.

It was Rick alright, but he was sitting in the driver's seat with his pants opened and his eight inch masterpiece of circumcised man meat just laying exposed against his thigh. I quickly got in the car with a huge smile on my face.

"We're not going far. I figured you could suck me on the way," Rick said in a gruff voice.

"Hell yeah!" I mean, there was certainly no way I was going to just sit next to an exposed cock and not put it in my mouth.

I gladly leaned over into his lap and took his warm penis in mouth. He moaned as I massaged his member with my tongue and my lips. He tasted so good and I couldn't wait to taste his yummy load. While I gently bobbed up and down on his shaft, Rick started driving us to his secluded spot.

Obviously I couldn't see anything, but I could feel the car moving and stopping and occasionally turning. Rick kept one hand on the wheel and the other on top of my head controlling my rhythm. From time to time he would firmly hold my head in place, and at just that moment the car would hit a bump and his cock would go deeper in my throat making me gag. I laughed to myself; he's doing that on purpose.

I worked my oral magic on his hot rod as he weaved through the streets moaning in pleasure. Eventually, I felt the car make a hard right turn and then the road got really bumpy. I wondered where the hell he was taking me, but it didn't matter. I was as happy as can be giving him road head. The road was so bumpy that he was regularly stabbing his cock down my throat. I choked and gagged and at one point thought about spitting his cock out and telling him that if he kept it up I would end up puking in his car, but I stayed where I was, devouring him. Honestly, I don't think he would've let me up anyway.

After a couple more turns, the car came to a stop and Rick put it in park and turned it off. He let me continue to suck him for a minute before telling me to get in the backseat.

"Be sure to push the passenger seat all the way up first," he instructed me.

I reached for the lever to adjust the seat and looked out at the surrounding area. Man it was dark. I got out of the car and quickly looked around; where the hell are we? We seemed to be in a wooded clearing of some sort. There was nothing and no one around. It was definitely secluded.

I got into the backseat and immediately leaned over and took Rick back into my mouth. I picked up right where I left off, bobbing up and down pleasuring him with my mouth. He reached out and began to massage my ass through my shorts. It felt so good!

"Damn, you've got a cute little ass."

"Thank you," I said, briefly pausing from the blowjob.

"I know you said no anal, but how about you slide those shorts down a little so I can see it?"

I thought about it for a second, but I really didn't care if he groped me or not. I thought it was super hot.

"Mmm.. okay!"

I raised up and fumbled with my button for a second. Then, I opened my shorts and pulled them down just a little bit. Rick immediately slid his right hand into the waistband and pushed them down even further just below my ass. He moaned as he began to squeeze my butt cheeks with his rough hands.

"Mmm, I like that cute little thong you got on."

"Thank you." Now he had both hands on my ass groping away and pulling my cheeks apart.

"Why don't you slide up between the two front seats and let me get a better look at it real quick"

Seriously? I was slightly annoyed. All I wanted to do was swallow his load, but he persisted and I didn't really seem to know how to say no. "With a giggle I said, "okay, but NO anal."

"I just want to see it, sweetie."

I crawled up over the console between the two seats and stuck my ass in the air giving him a perfect view. He immediately yanked my thong down to my thighs with my shorts.

"Fuck, that's a nice ass," then he buried his face in my butt. I could feel his coarse facial stubble against my smooth skin as he circled my anus with his tongue.

"Oh my!" It caught me off guard but it felt incredibly good. I didn't want him to stop. "Mmm!"

He poked and prodded my virgin hole and before long, his slippery tongue was inside me. He was tongue fucking me now and it felt incredible! I could hear him spitting on my anus and devouring me as he massaged my ass with his hands. Then, I felt a finger pushing into me.

"Agh! Wait!"

"I just want to feel how tight you are."

"Be very gentle."

He pushed his finger into me as I tried to relax. He had big fingers, much bigger than mine, but he did manage to penetrate me with a little bit of spit and a little more effort.

"Aghhhhhh."

"Nothing like a tight virgin hole." He was finger fucking me at a steady pace now. "You like it don't you?"

"Ugh yeah," I whimpered. Then, he inserted another finger. "Oh shit!" I lunged forward to get away, hands now on the dashboard. He pushed his two middle fingers in to the second knuckle as I squirmed and tried to resist. "No no no!"

"Just relax."

"Oh god," I cried as he now worked the two fingers in and out of me.

"There you go." I bit my lip, breathing heavily. I had never let a man get this far before. "If you can take two fingers then you can take my cock." I was silent. "Let me fuck you."

"No, I'm not ready yet," I said shaking my head. Then I said, "Besides I don't have any lube," thinking that would settle the discussion.

"Reach over and open my glove box." Oh no, I thought, he has lube. I opened the glove box and sure enough a tube of Astro Glide was in there.

"No, I- I'm sorry. I'm j-just not ready." I pleaded.

"Haha, I get that," he leaned in close to my ear, fingers buried to the hilt in my bum. "But what you need to understand is that you don't know where you are since you had your face buried in my nut sack on the way over here. So, it seems to me that you really don't have a choice but to do what I want. I'm not taking you back until you let me fuck this ass."

"What!" Was he fucking serious? He was right, I didn't know where we were, but would he seriously leave me here. I was a little panicky now. "Y-you can't be... serious!"

"Oh I'm very serious. I was clear about what I wanted in my ad." His voice sounded sinister now. I couldn't believe this was happening. "Now, get out of the car and come over here to the driver's side. And bring the lube with you."

He removed his fingers from my hole and got out of the car. I was stunned. Is this really happening? Dazed, I grabbed the lube and climbed out of the car on the passenger side, pulling my shorts and undies up. Reluctantly, I walked over to where he was standing by the driver's side door. He looked very serious now and he was stroking his throbbing cock. It looked bigger than ever now, and all I could think about was how it was going to split me open. My knees were shaking as I handed him the lube. It was still so quiet, so dark, and so lonely in this hidden place.

Rick pointed to the driver's side door. The window was down and he instructed me to lean into the car bending over the door. In shock and disbelief, I did as ordered. There was no use in resisting him. He was way bigger and stronger than me. I had to accept my fate and give him what he wanted.

As soon as I leaned into the car window, he yanked my shorts and panties down and pushed me against the car. My limp dick shriveled up even more as it pressed against the cold car door. Then, I felt his tongue jabbing at my anus once again. It still felt incredibly good, even if he was about to forcefully sodomize me.

"Mmm, don't worry. I'm sure your perfect little hole will have me cumming in no time."

I didn't know how to respond to that. I was scared, nervous, and even a little excited. Part of me figured that I may never have gained enough courage to give up my virginity, so maybe he was actually doing me a favor. He was forcing me to take the next step.

"Please, just be gentle," I whimpered nervously.

He didn't respond, he just began to rub some lube on my rose bud. It was cold at first and I jumped when he touched me. He worked his thick finger around my hole in a circular motion and slowly inserted it. Then he applied more lube to his finger and did it again. I was trying hard to relax, but my heart was racing. I could hear him rubbing lube up and down his shaft. I reached out and grabbed ahold of the parking break beside the console, bracing myself for the inevitable.

"Just relax," he said in a monotone voice, as he pushed his mushroom head against his target. I could feel it starting to force my anus open, but I was soo tight. His cock head breached my o-ring, and it hurt so much that I raised up on my tip-toes in an effort to get away. This made his dick pop out which made him angry.

"Stop pulling away damnit!" He spanked my ass very hard and put his hand on the small of my back angrily pushing me down against the bottom edge of the door window and effectively pinning me there. I couldn't get away from him now.

"You're getting this dick. Now, relax and open that fucking ass for me."

He spit on my butthole then, once again, he pushed his cock head against my sphincter, only this time he wasn't being slow or gentle. This time he forced his cock into my asshole, the thick head stretching my anus wide open until his tip finally made it inside. I kicked and screamed as he just held his cock there just inside my ass.

"FUUUCK! Oh shit! It's too big!"

He just stood there, holding me in place, letting me kick and squirm.

"Shhhh, calm down. The head is all the way in. That's the biggest part. Now, you have to relax or this is really going to hurt." His words sounded almost as though he cared about me and wanted this to be a pleasant experience for me. But the tone in his voice said that he didn't give a damn if it hurt or not. He was going to fuck me raw and that was that. He pushed deeper into me.

"Ohhhhh fuck! Aghh! Ple-pleeeease! No!"

He was completely ignoring me now and shoving his cock deeper and deeper until finally, "there you go. It's all the way in now." His voice seemed to be full of pride.

"You ready to get fucked," he asked as he gripped my hips.

"No, ple-," before I could even finish my futile plea, he pulled his rock hard cock back and thrust it into me. "Aghhhhhh! Ungh, ungh, ungh!"

He was really fucking me now, driving his cock in and out of my stretched little hole. I struggled but couldn't get away from the pummeling I was receiving. Being bent over through the door made resistance impossible, and I think that was the point. He had thought all of this out. I grabbed for the steering wheel, the gear shifter; I groped for anything, any way, to pull myself away from his thrusts, but it was no use. He was having his way with me.

He had pumped his cock in and out of me for at least ten minutes, while my dick slapped against the side of the car. I could feel cum dripping out of me. 'Oh my gosh, he's milking me,' I thought, as his throbbing penis was grinding against my prostate. It hurt so much getting forcefully stretched, but at the same time it was starting to feel good. The more he pumped the more my pussy opened up for him.

"Yeah, you're taking that dick good now."

"Ohh fuck!"

It did feel a lot better now, and I was starting to forget that he had forced me to do this. Maybe this is what I really wanted. Maybe I knew this would happen. Maybe I'm just a dumb sissy fuck doll. The thoughts racing through my mind, along with the feeling of his hard cock drilling my no-longer-virgin ass was driving me over the edge. I had been gooning to sissy porn all day long thinking about sucking dick, and now here I was losing my anal cherry to a complete stranger who basically forced himself on me. It was too much!

My little sissy clit was now hard and pressing against the car door. Rick's thrusting was making it rub against the smooth body of the car, the surface of which was slick with my pre-cum. I wanted to reach down and stroke myself, but I couldn't. The pressure was building in my loins and I knew I would cum soon, but I had never had a hands free orgasm before, and I didn't know if I even could.

"Oh gosh! Oh fuck! I think I'm going to cum!"

"Oh yeah?"

Finally, I couldn't take it anymore. My body grew tense, I squeezed the parking break white knuckle tight, and my orgasm over took me.

"Shiiiiiiiiiit! Fuck! I'm cuuuuuming!"

I convulsed and shot my sticky goo all over the side of his door, and for a moment, I was completely oblivious to the thick hard cock stuffing my ass. I actually bucked against him, forcing him deeper and harder into me, but I didn't care. I was in a state of pure ecstasy, with wave after wave of orgasmic euphoria rolling through my body.

"Fuck yeah! I knew you wanted this dick up your ass, you little sissy butt slut."

My eyes rolled to the back of my head and my body went limp while Rick sawed away at my ass with even more gusto, as if my orgasm had motivated him to reach his own. I was slowly starting to come down from my cloud when Rick pulled out of my butt. 'He didn't cum already, did he,' I wondered.

"I think you need some more lube," Rick said, as he wiped up the cum I had just shot on his car and rubbed it on his shaft. "I'm going to put this cum back inside you where it belongs." Then, he shoved his cock into my now welcoming hole.

"Ohh shit," I called out from in the car.

Ricked started drilling my pussy again, determined to break it in properly and blow his load. The car was rocking as his body impacted with mine pushing me against the vehicle. I could hear his hips slapping against my ass making a sharp clapping sound. I could also feel his penis beginning to swell up even thicker and I knew he was about to blow.

"You ready to get your first load up your little pussy?"

"Yeah! Shoot your cum in my ass! Give it to me!"

"Ungh ungh grrraghhhhhh!"

He crashed into my ass furiously as he launched stream after hot stream of his semen deep into my bowels. He gripped my waist and convulsed uncontrollably for several seconds emptying his balls of their thick slippery nectar.

"Now, that's how you service a cock, sissy," Rick said, as he pulled his tool from my ass and gave my booty a firm smack.

I pulled myself up out of the car and Rick handed me a roll of paper towels he had in the back seat to clean up with. I wiped his spunk off of my ass and got my panties and shorts back on while he cleaned himself up.

"Let's go."

I got back into the car and he drove me back to the parking lot. On the way, I noticed that we weren't very far away from civilization. He had just driven back behind an industrial area. I wondered how he knew about that spot, but I didn't say anything though. I was silent the whole drive, trying to process what had just happened. He technically raped me, didn't he? But in the end, I enjoyed it. I was a bit confused.

We arrived at my car and as I was getting out he said, "See you next time."

Yeah, I thought, there will definitely be a next time!