I Prostituted Myself to a Bear

I managed to waddle back up to my dorm room. It was still dark outside at 5:15 a.m. so I was thankful but also glad because no one was up at that time.

In the shower, my feelings of lust returned as I could only think of Gary's fat dick and the way he used his hands and mouth all over my body. I still had marks from his teeth on my upper chest and my breasts were sore from him stroking and sucking on them. I bled from my ass and watched the water turn red as it circled into the drain. Looked like I was on my period.

A couple of days went by and I was having trouble staying focused in class as my ass felt so raw and I kept bleeding and spotting. I also couldn't stop thinking about Gary and was waiting to heal so I could see him again.

My friends teased me about my duck walk, joking with me about how I must have taken it up the ass. I could only manage a smile and would do whatever to avoid blushing. They had no idea how right they were. The bleeding and soreness weren't going away so I made the embarrassing trek to the health clinic.

The nurse was a mid-50s female, she looked like she knew bullshit when she heard it and so of course I was shocked that she didn't seem to believe my story that I accidentally fell back on a guardrail while I was skateboarding and caused rectal trauma and bleeding like a girl on her period. Regardless, she let me down easy, gave me some suppositories and told me to take it easy as she winked at me and I waddled out.

Things got better after a few weeks, my ass healed up nicely and I was back to my usual activities of going to the gym, etc. While I still thought about Gary, I was busy with school and I had made some new friends. The $300 I made from that night made me feel like I was balling but I went through that like water.

Back to poverty, I started wondering when the next opportunity would arise. One day, I was sitting in chemistry class when I and everyone around me woke up to a loud *ping*. I looked down and saw a text alert from a number with a local area code. I quickly turned my phone to silent and read the text.

"Ishaan - remember me? It's Frank here..call or text back, I have biz 2 discuss"

I sighed and my heart began racing again. My fingers trembled as I responded.

"Hey there. Yes, of course I remember you...and Gary." My heart fluttered and my stomach rolled around inside with butterflies as I texted Gary's name out. I could barely pay attention to my surroundings as I received a reply.

"Great...well I have more money for you to earn. We are ready for you tonight. You still stayin' at the same place. I'll pick you up 10p sharp. Wear those tiny little fuck shorts you from last time. LOL"

Tonight?!! I had a calculus exam the next day. Fuck. What was I to do?

"Ok...sounds good" was all I could muster. The same feelings of anticipation and excitement built up inside of me as I couldn't wait for class to finish.

I got back to my dorm and began the waiting game. I studied what I could for my exam the next day but could barely pay attention. Day rolled into night and it was almost 10 p.m. I had to toss the running shorts I had worn the first time around because there was blood all over the inner brief liner, but thankfully I had several pairs so I pulled on a fresh pair instead.

I was thankful once again for the cover of darkness and it was quiet outside this time because it was a weeknight and everyone was either studying or asleep. I walked over to the street corner where I saw Frank already parked with his lights off. The butterflies were doing hurdles in my stomach as I approached his truck and opened the door.

"Ya look great tonight! Real sexy!" Frank grinned. He looked creepy saying it and it gave me some feeling of apprehension but I was already in his truck and he started moving. There was no mention of how much money was to be made tonight or if Gary was going to be there.

"You doing good? I bet you bled for a while, like a bitch on her period, ain't that right?"

"I bled for a little bit, I hadn't ever had sex before, it was my first time," I said, my face beet red and looking down.

"Hehe...you all healed up down there? Ready for another? I know Gary raved about you, thought you were the prettiest little thing he's ever fucked. He wanted to keep you for himself, but we got to make money off of your sweet little pussy!"

I stayed silent and looked out the window until we got to the trailer. The butterflies were now roaring inside my stomach as the familiar site of the abandoned trailer park came into full view. This time, however, there was another vehicle parked outside the trailer, it looked like a 90s model Chevy Caprice Classic with 22 inch chrome rims.

"Is someone here?" I asked, my voice quivering in fear and concern.

"Your next paying customer," Frank responded. He parked and I immediately regretted coming here, but it was too late now.

"Whoever it is, I just have to fuck him and take my money," I thought to myself as I stepped out. My flip-flops kicked up dirt as I followed Frank in, my legs felt like jelly. The butterflies were colliding with one another violently in my stomach.

"Carlos! This is Ishaan, Ishaan, Carlos," Frank yelled out. Frank stepped out of my way to reveal a big black man sprawled out on the sofa, the same one where Gary had taken me just a month ago.

Carlos looked like he was in his late 60s, very large, his head alone was 2x as big as mine, he was wearing basketball shorts and some Timberland boots and a big long tee. He was bald with some grays on the sides and on the back of his head. His nose was thick and flat with massive nostrils. His forehead reminded me of the Klingons from Star Trek. The top of his head had wavy thick ridges and his ears had white hair sticking out. His eyes were small, his lips were thick and full and he had a smooth face otherwise. He grinned at me and I could see several gold fillings. His arms were thick, each was easily 2x as thick as my legs. His thighs were mostly covered by his shorts, but his lower legs looked like chocolate brown tree trunks. I remembered thinking Gary was big, but Carlos easily dwarfed Gary. In essence, this man was terrifying to look at. My legs felt like jelly before I entered the trailer, now I thought I was just going to pass out.

"Hi there! Carlos!" The giant stood up to take my hand gingerly before kissing it. "Oh gosh! He's got to be like 6'6 or something! I'm barely coming up to his belly!" I thought to myself.

"H-heyy...Ishaan..." my voice trembled as I spoke. I stood in front of him with my hands clasped behind my back as he continued to stare at me, his face full of lust and his eyes of mischief. I could tell he was undressing me with his stare, studying me and it was apparent that he was relishing the look of fear in my face.

"You here to give me some booty? Ain't that right, bitch? Some fine lookin' brown booty?!" He snickered as he plodded back down, his deep baritone voice reverberated through my body as I gazed at him, my eyes wide with fear.

I gulped, "Y-yes, sir."

"Sir...that's right bitch. You ever please a Black man before? You know how it is...once you go black, you never go back!"

Both he and Frank roared out in laughter. Carlos reached down and slid off his shorts to reveal a thick, black anaconda. It was easily 9" long and about as thick as the thickest part of arm. It's single eye was already dripping as it moved around, looking for food. Carlos had trouble pulling it out all at once just because of its length but he began waving it as he grinned at the terrified look in my face.

"He's paying $500 to fuck you, sweetheart. He has to pay more because he's Black," Frank said, his voice more of consternation. "Not many folks are comfortable fucking a Black guy, so the price is higher. But you'll be good to him, won't you, Carlos?"

"Hell yea! C'mere sweety, come suck on this dick, show me how you can suck a mean dick!"

My legs felt like they were going to give out and I wasn't thinking clearly as I dropped to my knees first before realizing I was too far away so I ended up having to crawl to between his legs. "That's a sweet bitch, just met me and already crawlin'!" Carlos laughed out. Every time he spoke, it seemed like the walls vibrated.

Regardless, I managed to come up on my knees and make myself as comfortable as I could. I was wearing a light jacket tonight over my shorts. Carlos reached forward and unzipped the jacket all the way down and began stroking my nipples lightly as I began breathing heavy while trying to grab his penis. I bit my lower lip, trying to focus as I grabbed it and lifted it up from the base. It felt heavy and looked so long and thick in my little hand as I began to lick the head. The head was wet, the taste was familiar to me.

"Unnnhh...unnnhhh...that's it, go slow, bitch. I want to enjoy this, get my money's worth!" He cackled as he pinched my nipple in between his index finger and thumb. With the other hand, he grabbed his penis and started smacking my face and made me try to chase after it with my mouth. I felt so embarrassed, but he only laughed at me, before finally letting my nipple go and grabbing my head instead and shoved it down on to the head of his penis.

I felt it grow and lengthen in my mouth, I could barely open wide enough to accommodate it. He pinched my nose shut as he shoved my head down harder. I choked on it several times and tears began streaming down my face as he wouldn't let up.

"Open wide, bitch, take it all!" He yelled out. His booming voice terrified me and I did what I could before he finally released me and I was able to blow him properly. I began to suck the head while stroking the rest of his penis, while occasionally licking the underside and then his balls. Oh, and his balls were the size of duck eggs and he was particularly responsive whenever I sucked on those.

I was busy giving this man I had just met a blowjob, I heard the bell ring. It was Gary.

"You fuck me and now you're on to your next fella! You're a horny little cunt! Only whores fuck Black dick!" Gary yelled out as the door slammed shut. He joined Frank on the little bed across from the sofa. He smacked my ass as he sat down.

I was so embarrassed but I kept sucking Carlos' dick and Carlos kept groaning and grunting, obviously pleased with the money spent thus far. I felt his body begin to tremble and shake deeply, as I felt him dig his feet deeper into the floor. "Ohhh...shit...ohhhhh...fuck...c'mere bitch...ohhhh...keep your mouth on there!" Carlos screamed out as I felt a burst of cum shoot out as he thrust his hips forward. There was so much cum. I couldn't contain it as he kept going, until it started running out of the sides of my mouth. He had gripped my head with both hands, so there was no question of escaping.

His orgasm lasted longer than I could have imagined but he eventually finished, and he let out a deep satisfactory groan and collapsed back on to the sofa. I kept my hand on his penis which was still semi-erect and made sure to swallow as much as possible and continue to suck and lick the head to make sure I got every last drop as I looked at him. My breasts and belly had cum on them and some of it had dripped on to my thighs and shorts.

I slowly got to my feet, still wiping my face when he reached out and grabbed my arm, "We ain't done yet. I got to fuck you next!" He ripped off my jacket. "Drop them little shorts and get up on here!"

I dropped my shorts as he was told, revealing my long slender legs, my 7" penis in full view. His cum was all over me, on my chin, my chest, and my thighs. Frank tossed him the lube bottle as he lathered his penis with it while stroking himself back to a full erection. I was surprised by his virility, as he had cum only moments ago and he was already back to a full erection.

I straddled him and my belly button touched his face as he reached around and guided his dick into my hole. I screamed out. "Arrghhh...noo...nooo...fuck you're huge!"

He paid no attention to my screams as he gripped me with one arm around my waist and his dick with the other as he kept pushing me down. I kept screaming through gritted teeth, begging him to stop but it was too late. His hands were on my hips as he kept pumping me down on to his manhood. My hands gripped his arms for dear life as I kept screaming. "Unnnhhh...unnnh.....aarrghhh...oh God!!"

"Too late, sweetheart! You're about to get bred by Carlos!" Gary snorted a laugh. I was sweating bullets from the pain and trauma he was inflicting on me. Carlos definitely felt bigger than Gary did, I didn't remember Gary being as painful going in the first time.

Carlos made me feel like a virgin. Finally, all 9" of him were inside of me. It felt like an achievement of sorts, finally feeling his balls up against my ass. His massive dick felt like it was in my colon. Thankfully, the pain went away soon after. I suppose it was a benefit of no longer being a virgin. My chest was closer to his face, more specifically, my breasts were close to his waiting mouth, he began sucking on them as he held me tight around the waist and we began reciprocating movements. I started bouncing up and down while he kept thrusting himself up. Our moans and groans filled the room. I wrapped my arms around his big head as he licked my nipples and nibbled on them.

It was not much longer after that when I let out a shriek, "Ohhhh...I'm cumming...ohhh gosh...I'm gonna cummm!!" Carlos didn't flinch as he kept fucking me. Whatever I squirted out was on his belly. I was breathless and exhausted but he kept going. In my state of exhaustion, I failed to notice that Gary had stripped down and was standing behind me. Without warning, Carlos grabbed me around the waist and held my ass up while Gary began shoving himself into me.

"What the fuck! Oh God...noo...nooooo....arrghhh!" I shrieked again, my teeth gritted. I had 2 dicks inside of me and felt my asshole was being ripped apart. In an effort to deaden the pain, Carlos had never stopped sucking on my breasts, but it did little good. I had forgotten how big Gary was but he just gave me a rude reminder.

I gave up struggling as I was sandwiched in between both large men. I just held on to Carlos' massive arms for dear life as I was pounded into oblivion. Both men came at the same time as I heard loud screams and grunts coming from both. I felt warm liquid shoot up inside of me as Gary intensified his pumping motion. Once they both finished, Gary pulled out and Carlos threw me off on to the sofa next to him as they both shoved their dicks in my face.

"Stroke 'em clean, put 'em in your mouth and clean 'em off!" Gary commanded. I immediately did I was told. I felt like I was going to pass out but I managed to finish them properly and lay there, completely spent. I had cum pouring from my asshole, I had cum on my face and chest.

Frank tossed some dollar bills on to my chest. I picked them up and stared in horror as it was $200 I was holding.

"You were supposed to have sex with Carlos only. The deal was never for Gary to get involved," Frank said with a smile. "You owe Carlos another session, and if Carlos has a homey he wants to bring along, you fuck him too and whoever else we want you to fuck!"

This time I didn't even pretend to try to dress myself. I just got into his truck, my ass bleeding and dripping with cum. I admitted to myself that I was a full-on prostitute. There was no going back.