Jake Savage Diaries: The Addiction

She looked up and saw her boyfriend stroking his cock. "Fucking loser," she said but the vision of him masturbating made her cum for the first time.

You could tell she had no experience cumming hard. She gasped and her legs shook for a moment but there was no big explosion. A few drops of cum dripped on the dirty floor, leaving clean spots behind as they landed. I gently grabbed a handful of hair and pulled her head back as I fucked her harder.

She started breathing deeper and I felt her loosen so my cock went in and out of her easily. I gave her a slap on the ass to make her pussy spasm. Her boyfriend jumped from the loud noise but soon went back to stroking his cock.

I slapped her harder, this time the spasm triggered her and I felt her cum again. This time she got up on her tiptoes to let me get just a touch deeper inside her. I reached around to rub her clit and she let out a guttural moan.

She knew what she liked, and she tightened as the tension inside her grew. I pulled her hair harder and started firmly thrusting my cock inside her. "I love that I don't even know your fucking name," I told her as my balls slapped against her ass."

She moaned again and said, "Shut up and fuck me."

I spread her legs apart further with my feet and started ramming myself inside her. She cried out like she was in pain and her boyfriend started to get out of his chair when he heard her saying, "Fuck me, fuck me."

I looked right at the boyfriend and nodded for him to take his seat. I took my time banging his bitch. My balls slapped into her for the next 10 minutes. I was sweating from all the effort and her pussy kept getting tighter. He kept stroking his cock and I thought you don't deserve her pristine little cunt.

Her pussy was bright read now and looked sore when, she cried out, "I can't take much more!"

My cock swelled in anticipation of cumming, I leaned into her with all my weight and grabbed the edges of the desk so she was pinned. She arched her back, "Too fucking deep," she groaned.

She was right; I was a long way inside her. She tried to get away, but I kept her pinned. She couldn't go anywhere and forced my first shot of cum into her cervix. She whimpered and tried hard to escape again. My cock flexed inside her violently and I shot another load into her core. She cried out in pain.

Her boyfriend leapt out of his chair, "Get off her!" he yelled.

"Sit the fuck down!" I yelled back at him.

He stood there and watched her whimper as I finished shooting my load into her. My cum ran down the inside of her legs and she was on the edge of tears. I pulled out and more of my cum dripped onto the floor behind her.

Her pussy was gaping open as I reached down and pulled up my pants. I zipped up and did up my belt. I slapped her on the ass, "You have a great pussy, too bad this life is gonna fuck it up forever." I told her.

She didn't say a word.

I reached for my wallet, took out 100 bucks and slipped it into her hand. "Enjoy getting high; you earned every minute of it." I told her.

The boyfriend was looking at her lying across the desk like she had been raped, "You finished, asshole," he said.

I was tired of him thinking he was in charge. I took out another 100 and threw it on her back. "Clean her up," I told him pointing at her pussy.

He tried to look intimidating.

"Get on your fucking knees and clean her up or I'm going to fuck her again even harder." I told him. He knew I was serious.

She finally started to respond and turned to her boyfriend, "Darryl, just do it, don't let him fuck me anymore." she said.

Darryl grabbed the money off her back. He thought about doing something for a moment before stuffing it in his pocket and kneeling. I went and sat in his chair to watch him clean her pussy.

He pulled her ass cheeks apart and started licking her. At first, she was quiet but she started moaning as he went deeper. I saw her adjust her hips for his mouth just like she had done for me. I kept watching him lick cum out of her, and her body writhing in pleasure as he did.

She reached down and started to play with her clit again and I saw her shudder as she came for his tongue, it made more of my cum to leak out from deep inside of her. He continued to lick her and started stroking his cock again. I loved how pathetic he looked kneeling there.

As he got harder his licking got faster. She reached behind to pull his head into her pussy by his hair, burying his nose in her ass. He groaned loudly and he came under the desk and her legs began to shaking as she joined him. He did more than clean her, he drained her. My need to punish him further was satisfied.

He got up and stumbled over to the couch and sat down without breaking his fall, his now soft cock still in his hand and both legs of his jeans were wet with cum from all of us. She stayed spread on the desk and dripped for a while as she caught her breath. Eventually, she joined him on the filthy couch.

She cuddled into him and even with her knees closed I could see her pussy peeking out, still swollen and wet as it leaked onto the cushions.

I got up from the chair and stood in front of them like a used car salesman. I took 400 out of my wallet and fanned it out so they could see it all. "I'll be back tomorrow for that ass," I said pointing at her naked pussy."

"Fuck you," she yelled at me.

"No, sweetie, I'm gonna fuck you," I said back, "If you don't want the money, don't be home. I'm sure there's another hottie who could use 300 for one night in her ass."

I put the money away and went back out through the kitchen. Just like the night before the house was eerily quiet as I waited for my Uber back to the hotel.

The next day at the conference flew by. It wasn't until the day was over and I was enjoying happy hour that I put some thought into what I wanted to do on my last night with the hot tramp and her loser boyfriend, Darryl.

I stopped at a downtown sex store and got a tube of anal ease. Then I hit the grocery store for a 6 pack of beer. I wasn't sure what was going to happen tonight but I wanted to be prepared. I had plenty of money in my wallet and headed to Southie. I figured my odds were 50/50 at best.

When I got there the house was quiet and the living room was empty. I thought I had must have found his breaking point and he wouldn't sell me her ass. I sat down in Darryl's chair and cracked a beer open. Looking around the room I couldn't believe people lived this way. It was disgusting, wrappers and garbage everywhere. They were never getting out of this life.

I finished my beer and flung the bottle against the wall, instead of smashing, it got stuck in the wet drywall and I laughed as it hung there. I cracked another beer and stated to make a plan to find some alternative pussy when I heard the kitchen door open.

The two of them stumbled in both high and drunk. "What the fuck are you doing sitting in my chair," Darryl yelled as he came over to me.

I stood up, and looked at his eyes, he was wasted. "I'm here to fuck your girlfriend," I told him.

She laughed when I said it and leaned over the desk, hiking her skirt up. Her ass and her pussy were bare. "Look at me," she giggled, "I'm a fuck doll."

Darryl stumbled past me and sat in his chair. He grabbed one of my beers and cracked it open. "Go ahead, fuck her, I'll watch," he laughed.

"Hey," she said, "Why do I have to be the one who gets fucked every time?"

"Because you're a Fuck doll," Darryl said. They both laughed like it was the funniest thing they ever heard.

I wasn't amused and I walked over to the end of the desk where her head was and undid my pants, pulled my cock out and started stroking it in her face. I heard Darryl unzipping his pants and turned to see him pull his cock out. He looked up at me, "Fuck her good," he said.

She seemed very turned on by seeing two cocks getting hard for her and opened her mouth for me. I slid my cock in as she reached down with one of her hands to play with her naked pussy.

She wasn't nearly as tense this time, her mouth slid flawlessly up and down my shaft, she used plenty of spit and I felt the need to resist a bit as her new relaxed drug whore skills were impressive. I looked over at the boyfriend and he was enjoying everything he was seeing.

Even when I grabbed her by the hair and fucked her face harder, neither one of them reacted. It wasn't until I heard her moan and watched cum dripping down her leg that I decided she was high enough to fuck all her holes tonight.

I still wanted to screw with Darryl's head so I told him to lie down on the sofa so she could suck his cock while I fucked her. His eyes lit up and quickly moved to the sofa and laid down. I pulled my cock out of her mouth and led her over to him. I made her straddle his face then lean down and suck his cock. I stood back and watched them 69.

He was licking her pussy like it was full of the heroine he so loved and she sucked his cock so deep I was a little jealous that I hadn't tried to throat fuck her myself. I sat in Darryl's chair and popped another beer as I stroked my cock and watched them a little longer.

She looked up and saw me stroking my cock. An evil smile came over her face and she pulled her arms into her dress and slid it down, exposing her cheap white bra. Reaching behind her back, she clicked it open and let it slide off her arms onto the floor.

It was the first time I'd seen her naked tits, they were small but firm. Bright white triangles of skin surrounded them where the sun couldn't reach. She pinched her hard brown nipples between her thumb and index fingers as she looked at me and rode Darryl's face.

She shuddered again and I assumed it was another mini orgasm. Once it ended she pointed at my groin and mouthed, "I want your cock," before leaning down to suck Darryl again.

I stood up and took my shoes and pants off, grabbing the lube from my pocket as I did. My cock was hard and I wanted to nail that bitch. I put one knee on the sofa next to Darryl's head and looked down at him licking her. He saw my cock coming and shifted his tongue to her clit to avoid it.

Her pussy was swollen nicely from the licking and I slid right in. Her warm young body wrapped around my cock and squeezed it like a long lost friend. I slowly began to fuck her and laughed to myself when my balls slapped Darryl in the forehead.

I teased her with the head of my cock and she came again, this time a little harder. As soon as I felt it, I slid all of me inside her; she arched her back and pulled off Darryl's cock. "Fuck it's big," she breathlessly muttered as I held it inside her to stretch her out.

I pulled open her ass cheeks with one hand and squirted plenty of lube on her dark little anus. She turned around and said "No," while trying to push the lube away.

I used my thumb to gently rub the lube into the opening of her ass while staring into her big brown eyes. She turned back to Darryl's cock and sucked it while I continued to fuck her pussy and add pressure to her anus with my thumb. I added more lube as she loosened up. I pressed the tip of my thumb inside her.

She turned back to me again. I expected her to say "No," but she said "Don't cum there." before she went back to Darryl. I pressed the rest of my thumb inside her and held it still so she could adjust. Her pussy was extra tight with my thumb inside her and I used it to rub my cock as I slowly penetrated her over and over.

Once she relaxed enough I slowly pulled my thumb out and squeezed more lube in the small gape that was in her ass now. My thumb slipped in easily the second time. The numbing lube was doing its work as she relaxed completely. A few minutes later I could fuck her with ass my thumb and her pussy with my cock at the same time.

I could hear Darryl getting close so I pulled her hair hard enough to get her off of his cock. "Lick his balls and make him work for it." I told her and she obeyed every word.

Darryl was still licking her pussy but I could hear the frustration in his sounds now that his cock wasn't being sucked. I looked down and enjoyed the view of him pouting as I pulled my cock out of her wet pussy and dripped some of her cum on his face.

I took my thumb out of her and ran the shaft of my cock between her ass cheeks. She was missing the fullness of having my cock in her, and started bumping me harder and harder with her ass as I fucked her crack.

My cock was getting numb from the cream so I pushed her away far enough get the tip right outside her slightly gaping anus. I let her bounce on it for a few moments before telling her "Push it in."

She tried a few times but my cock kept falling out of her little hole. I lined my cock up with my hand and held it there firmly as I used the other hand to guide her ass onto me. There was a small "pop" as her sphincter further relented and I was inside her.

I thought she would scream or cry but she just kept sliding it inside her until I felt her hit my pelvic bone. She moaned loudly and I tried to force it in even further. It was so tight I was sure it was hurting her but she seemed to be enjoying it.

I stayed still as she pulled forward and slammed her ass into my groin over and over, getting more aggressive with each thrust backward. Even partially numb it felt amazingly erotic to have that tight ass wrapped around me. She moaned like a wounded animal as she milked my cock with her ass.

Slam, slam slam, she continued until I couldn't take it anymore, I had to cum so I grabbed her by the hips and started drilling her ass. She had loosened up so much I thought I might be in her pussy. No matter how hard I went she kept her ass up in the air and she took it all.

"Suck his cock again," I told her as I felt myself on the edge of cumming. She barely licked his head when he came in her mouth. She was surprised by it and gagged hard when it shot into her throat. Her asshole tightened as she gagged. I pushed her head right down on his cock and she gagged again. This time the feeling of her asshole pulsing so hard set me off and I drilled a huge load of hot cum deep into her ass.

I pulled out after the first load and fired the next one into the gaping hole I had left behind. She tightened, arched her back so that her nipples were in the air and orgasmed in Darryl's mouth. This was her strongest orgasm ever and he coughed as he tried to swallow all the fluid.

The next two short ropes I shot on her pussy which ran down into Darryl's open mouth. I couldn't resist when I saw it happening and I milked the rest of my cum into his mouth without him even touching me.

Eat that fucking loser, I thought.

I felt amazing and slowly got off the couch. Darryl tried to get up too but his girlfriend never moved. "You ok Crystal," he asked from underneath.

She turned to look at me "You came in my ass," she said with panic in her voice. "No one's ever cum in my ass."

I found my pants, grabbed my wallet and handed her 300 bucks. "In this world, when someone pay's for your ass, that's exactly what they're gonna take Crystal." I told her.

She looked at the money and then down at Darryl before getting up. Darryl's face still had cum on it from us and he wiped it on the filthy sofa. "Give me half," he demanded.

She ignored him and got up. She went over to his chair and sat down still looking at the money and looking at me. "What's your name?" she asked.

"Jake, my name is Jake," I replied.

Darryl got up and went over to demand half the money again.

She looked up at him and then back at me. "Jake, what will happen to me after this money is gone?" she asked.

"If you stay here, he will sell your ass until you are die alone in an alley," I told her.

He looked at me like I was stealing his golden ticket. "Shut the fuckup." he growled.

"What would you do?" she asked me.

"Find a man who would never sell your body or eat another man's cum to feed his sickness, that would be a good start." I told her.

"You're had your fun now fuck off." He yelled at me.

I'd had enough of his bullshit, I had humiliated him every chance I got and nothing changed. "I'll pay you 500 bucks for her right now," I said.

He paused, "700," he said.

"500 and you go get high with it," I replied.

I got the money out of my wallet and he took it immediately. He didn't even look at her as he disappeared out the kitchen door. She yelled "You're an asshole." as he left.

"I can get you home again you know," I told her. She began to cry.

The uber trip to the train station was quiet. I made her phone her parents to tell them to pick her up when she got there and got her some dinner. We sat on the train platform and she asked why I was being so nice.

I told her I owed it to her for cumming in her ass, and a lot of other things I did to hurt her. I admitted I enjoyed being the first man to violate her ass and fuck her like a doll. She touched my arm and said, "Most of it felt really good, but next time let the girl know so she can be prepared."

I finally got back to my hotel and took a long shower. As I fixed my hair in the mirror after I had one awful thought, "I'm probably more sick than they are."

It was over 5 years before the conference returned to Boston. I headed down to Southie on my first night to see if Crystal had returned. I searched most of the night and saw plenty of girls but none of them were her.

It was around midnight when I started walking home and a voice in the shadows asked, "need a blowjob."

I knew it wasn't her voice so I asked "Hey, do you know Crystal?"

A skinny man with rotten teeth wearing women's clothing stepped out of the alley into the light and I had a good look, "Hello Darryl," I said.

"Did you find Crystal?" he asked?

"No, have you seen her?" I replied.

"Not since the night I sold her to you," he said, looking down at his feet in cheap women's heels with torn pantyhose.

I gave Darryl 50 bucks, "Go get high Darryl, I'll take a raincheck on the blowjob."

It was the last time I'd ever visit Southie.