Jake Savage Diaries: The Addiction

My real life is completely predictable. I've been married forever, kids are grown and educated, living on their own. My wife and I have sex occasionally, but we can take it or leave it. She has limits and that's my reality. If I want to experiment, I know she won't be the one I'm fucking.

I own a franchise, which one doesn't matter. They are all the same, I buy their shit resell it and give them a cut. The business run's itself that's why I bought it. Well, that and the quarterly conferences that get me out of town for a few days. When I'm in a new city all by myself, I don't have to be a tight assed, upstanding franchisee. I can be anyone I want to, and that usually means Jake comes out.

I could spend a lot of time describing Jake, but the best way to learn about him is to tell you what happens when there isn't anyone around to keep him in check. I know he's who I really am deep down, but I'm more comfortable thinking he's just a temporary alter ego.

The company's kick of conference was in Boston this year. It's one of my favorite City's for the bars and seafood. If the Sox are in town, it's usually worth a trip to see the green monster, or at least grab an 11-dollar hot dog and beer. This year they were on the road in New York, so I knew I'd be looking for my evening's entertainment on some street corner in Southie.

I checked into the Hilton downtown on Sunday and unpacked. The conference was a 4-day affair, so I'd have 3 nights for Jake to find the kind of pussy he liked. It was a warm summer evening that first night, so I went for a walk to find an oyster bar. It didn't take long to find O'Neil's right in the center of the City.

O'Neil's was a traditional Boston Irish pub with snugs to sit in if you wanted privacy and plenty of brew on tap. They took my order at the bar and my oysters and beer were on their way. I loved Boston for being a place where eating at the bar was normal. A huge plate of oysters arrived in a matter of minutes, and I listened to the banter of the punters around me as I slurped down a dozen.

I'm not a huge fan of the taste of oysters, but they make me super fucking horny. I don't understand how they work; I just knew after eating them I wanted to fuck everything in sight. It was part of becoming Jake, I would never make the decisions he does, he likes extreme situations and the hornier he got the less he thought about the consequences.

After finishing my oysters and the last sip of beer, I paid the bartender and headed out onto the street. It was after 9 now so the sun was down, and I could start exploring the night. The oysters were working, and Jake was getting turned on by every set of sexy legs that walked past him.

Not wanting to waste any more time, I grabbed an Uber and headed for Southie. I knew Jake wanted to look at the wildlife down there, it's a tough part of town, perfect for hunting. The cab dropped me on 8th street and I headed toward L. Southie is where the working class, the whores and the pushers ply their trade.

I knew I'd find some "street meat" down there and easily get my cock sucked. It didn't take long before I found a couple women who offered those very services.

As soon as I saw them, I felt Jake take over. He wanted to find the biggest slut in the city and he had a lots to choose from. As I walked over, I was approached by two women who asked if I was "Looking for a date?"

The first one was tall and super thin; you could tell she was a crack whore and her smile showed the rotten teeth of a long time user. There was no way she was touching my cock. Her friend was better, 40ish, but could have been 20 in reality. Long dark hair and a short blue jean jacket that she had opened so I could see her tits. She had a short tight pink skirt on and long legs with torn pantyhose. Well used platform dancer shoes made her much taller than she really was.

I asked her how much for a blow job, and she replied "20". I grabbed her arm and saw then track marks of a heavy user. She pulled her arm back and said, "get the fuck off me". I laughed at her and kept walking. I could hear them yelling "Freak!" Even though I was a block away.

"Go make someone else sick you fucking skanks!" I yelled back.

I'd made it all the way to "J" before I saw another street worker. Unlike the last two this one didn't approach me at all. She was leaning in the doorway of an abandoned store and had her head buried in her phone. The light off her phone gave me a good look at her face. She had short dark hair and a face that reminded me of Sandra Bullock when she was younger.

She wore a short black dress that was almost transparent from the waist down. Silver chrome heels that were polished up and bare but well-tanned legs make her look fresh and young. Even her small purse looked new and matched her shoes. I knew she hadn't been on the streets for long. I asked her, "How much?"

She looked up from her phone and gave me a good look up and down. I was in my 40's but still very fit. I could see her checking out my shirt logo and jeans, she even checked out my shoes before looking up at me again. Once she decided how much I could afford, she said "30."

I stepped forward and took her arm gently to check for needle marks, there were only a couple. She didn't pull away and let me have a good look. "Smile for me," I told her.

"What the fuck for," she replied tersely.

"I wanna see if it's just needles or you smoke the pipe too," I told her firmly.

"What do you care what I fucking smoke, you want a blowjob or don't you." She fired back.

"Let me see your teeth or you lose 30 bucks," I told replied.

She smiled and wagged her head at me "good enough?" She asked sarcastically.

Her teeth were still good, but I knew to wouldn't last. The faint stains were starting and in a matter of months they would be rotten. "Do you have a place?" I asked.

"The alley," she said pointing across the street at a gap between two houses.

"Not for 30 bucks," I said, "You want the extra 10 we need a place,"

She paused, trying to think of what to do.

"I'll give you 40 if you have somewhere private," I offered, "40 bucks is double the street price and I know you can score some snow with that."

She started walking down the street and I followed. We went through a couple empty lots and under a fence. I assumed there was a chance we might get mugged but my alter ego Jake wanted his dick sucked, so I went where he told me too. We ended up behind a row of beat-up houses that appeared to be abandoned. There was a short wooden stairway into one of them.

We entered the kitchen. Garbage covered the floor and the counters. I noticed a couple of cupboards had the doors ripped off and the light on the ceiling was smashed. The walls had food splattered on them. No one had cooked in there for a long time.

We went down a short hallway into a living room that was lit by a single bulb on the ceiling. A beaten-up couch and desk were in the room and some guy was sitting in a lazyboy that was covered in holes and burn marks. As soon as we got in the room he yelled, "Who the fuck is that!"

The girl looked at him with a scowl, "He's a trick,"

"Who the fuck told you, you could bring a trick here you stupid bitch," he bellowed.

"He told me he'd pay 40 if I had a place." she said angrily.

The guy stood up and came toward me. He was over 6 feet and looked mean, I wasn't sure if he was going to hit me. "Give me the money!" He demanded, as he held out his hand.

"You aren't getting shit until I get my cock sucked," I told him firmly.

He looked at me hard and I stared right back, daring him to do something. I was way smaller, but I wasn't afraid of him at all.

He went back to yelling at the girl, "This is why you don't bring your fucking tricks home with you, this guy is probably broke. I can't understand how you can be so fucking stupid." He bellowed at her.

"We need money if you want to score tonight you fucking asshole, it's dead out there," she yelled back.

"Well, if you would suck more cock and spend less time on your fucking phone maybe we could score, ugly cunt." He growled at her.

"Fuck you!" She yelled and hopped up on the desk so she could look at her phone again.

Once she was on the desk, the light in was bright enough that I got a really good look at her. She had great tan skin and amazing muscular legs, I thought she must have been a cheerleader before she got hooked up with this dick. Her body was thin, and she had small tits. Her face was very pretty.

Dark brown eyes and a small feminine nose gave her a runway model quality. Her mouth had full plump lips. I couldn't wait for her to stop fighting so she could use them to get to work on my cock.

The guy was really pissed now. He yelled at me, "How much you got? If you wanna fuck her it's eighty bucks."

She yelled back at him "Nobody's fucking me!"

"We need 80 bucks if both of us are going to score stupid," he yelled back.

"Then I guess you don't score then do you," she said sarcastically.

"This is my place moron, if you do anything here, I get a cut." He bellowed back.

"I didn't ask to fuck her, I just want my dick sucked," I interrupted. Hoping the arguing would stop and I could get what I came for.

"Take him upstairs stupid." He said to her, like a teacher scolding a child. "Then get back out there and earn enough so you to get high too."

I really disliked this bastard and felt like being a prick to him, so I asked him "Why don't you watch her suck my cock?"

He looked at me fiercely, "Do you think I enjoy making my girlfriend suck cocks so we can afford our dope asshole?" he said angrily.

Fuck him I thought, you wanna make her whore for you, you should watch.

"I'll give you 40 bucks to watch," I said it like I was closing a deal.

"You'll give her 40 to suck your cock and another 40 if I watch?" he questioned.

I opened my wallet and pulled out 80 dollars, making sure he saw there was lots more in there. "Eighty bucks, bareback blowjob, she can spit my cum out after I leave."

They looked at each other. "My forty up front," the guy said while looking at his girlfriend.

I handed him 40 bucks.

He went and sat in the chair again, looking at the money I gave him. "OK bitch, earn your 40." He said sternly.

She got off the desk and came over to me, squatted down and undid my zipper. She fumbled around with my underwear and located my cock. Once she pulled it out, she wasted no time putting it in her mouth.

I started getting hard right away. I was looking right at her boyfriend. He watched her head bobbing back and forth on my hardening cock. He looked angry as I grinned at him.

I noticed his girlfriend didn't stroke my shaft or squeeze my balls, she was an amateur. The blowjob felt great, but I could last all day getting head like this. I let her suck for a couple minutes so he could hear her slurping sounds.

"She sucks cock like my first girlfriend." I said to him while she worked. "She will get better after she's had a couple hundred dicks in her mouth."

I could see he was still angry but he didn't seem very tough anymore. I firmly grabbed a handful of her short dark hair and held her still so I could fuck her face. She gagged a little when I went deep.

"Good tongue skills, and only a little gagging, she's worth 40 bucks," I told him.

"Shut the fuck up." he yelled back, getting more and more agitated.

She pulled off my cock and spit on it a couple times before continuing. "Fuck you're sexy." I told her, rubbing her head like a good dog.

I resisted a little longer so I could enjoy looking down at those sun kissed legs and great chrome heels. Her black panties were on full display as she squatted, and I wondered how sexy her pussy was. Based on her blowjob skills it must be young and tight. I thought to myself, you should have fucked her.

My balls tightened up and I grabbed both sides of her head so she couldn't move. I gave her face a few hard thrusts and shoved my cock in far enough for her to start gagging. The first rope of cum shot down right her throat.

She tried hard to push me off, but I only gave her enough room for a quick breath before I shot another big load into her. She coughed and gagged as the rest of my cum filled her mouth.

I looked right at her boyfriend as I finished feeding her my last few weak ropes of cum. "Your girlfriend has some talent; she swallowed the first two loads." I said with a cocky grin.

Before I took my cock out of her mouth, I held her chin and made her look up at me. "Don't spit it out until I leave, or I'll be back for my 80 bucks", I told her. Then I gently pulled my cock out of her mouth.

"Get the fuck out of here!" her boyfriend growled in a rage.

"Fuck you! I told him, you sold your body, same as her." I yelled back.

He got madder and yelled at me "I didn't sell you my body asshole, I watched her suck your cock, now leave."

I wanted to teach this loser a lesson about selling his body, so I pulled 120 buckets out of my wallet. "If you want more money then swallow the load in her mouth, you can have it all." I said, waving the 120 at him.

She looked at him and shook her head no. He looked at the money in my hand. "That's 4 bags of snow for 1 fucking blowjob," I told him. "It's a sweet deal."

"You're fucking sick," he said to me.

I started to put the money away.

"Wait," he replied, "120 to swallow it."

"Yes, right after you swallow." I was daring him to do it.

She was shaking her head faster now. Her boyfriend snapped his fingers and pointed at his mouth. She stood up, walked over to his chair, and leaned over like they were about to kiss. He opened his lips wide. She was shaking as she let the rest of my load fall into his mouth. He swallowed quickly. There were ears in her eyes.

Without hesitation I handed him the money. She sat on the couch, staring at him in disgust and amazement, the room was silent.

"Leave," he calmly demanded.

"I put my cock away and zipped up my pants. "I'm in Boston for 2 more days. If you two want to earn more money, be here tomorrow night, I'll bring extra cash."

I walked through the kitchen and out the door. It was silent in the house as I stood outside waiting for my uber back to the hotel.

The next day I was looking forward to going back to Southie. Making that asshole swallow my load made me want to see how far I could push him. His girlfriend was very fuckable and I was going to use it against him every chance I got.

I loaded a few hundred in my wallet and once it was dark, I jumped in an uber.

Once I got there, I let myself in and headed to the living room. You could hear the two of them upstairs fighting.

"We can make a lot of money from this fuck!" He was yelling at her.

"Sure we can but, he's turning you into a fag!" she yelled back.

"I'm not a fucking fag, you stupid bitch, I did it for the money, we both got high after didn't we." he screamed.

"I don't like what he does to us, its fucking creepy!" She said, "who does those things."

"Shut the fuck up bitch, do you wanna get high tonight or not?" He barked.

She looked at him angrily without saying a word.

"Well, what's the answer, do you wanna get high tonight? If we score a couple hundred, we can get the good stuff!" he barked again.

"Yes," she said "Just don't let him fuck with you."

I heard them coming downstairs, so I went out the kitchen door and waited, pretending to just arrive.

They were both in the living room when I stepped inside. "Hey," I said when I got to the living room and saw him in his chair and her lying on the beaten-up sofa.

She had on the same black dress and heels from the night before. The way she was lying with one leg up, you could see her black panties. She clearly didn't care that I was looking.

He replied "Hey," and looked at her. She was looking at her phone again.

"You here for another blowjob?" he asked.

"No," I replied, "Tonight I want to fuck her,"

She put the phone down, "I don't fuck tricks," she said.

"I'll pay 120 dollars to fuck you right there," I said, pointing at the desk.

"She doesn't fuck tricks," he said.

"I guess you don't want the 80 I was gonna give you to watch then." I said to him. "I was hoping to spend at least 200 bucks tonight.

"Give us a minute," he said, and he waived at his girlfriend to go upstairs.

There were whispers and the odd "Fuck him," as the conversation dragged on.

"I don't want him cumming inside me," she said at one point.

"Would you rather suck 20 random cocks!" he replied.

They both came downstairs, "100 upfront," he said firmly, I gave him the money.

She was all business. She walked over to the desk, lowered her panties, and stepped out of them. Then she bent down, picked them up and tucked them in her bra before bending over the desk. She spread her legs and got out her phone.

Her boyfriend went and sat in his chair. I walked behind his girlfriend to check out her pussy. With her dress still on and her legs extended to the floor it reminded me of all those great summer nights fucking my wife on the hood of my car. Back when she would get wet enough I could nail her before her panties hit the floor.

This girl had a sweet young pussy. It had short brown hair on the lips and a little brown edge of skin around the opening. I wasn't sure what her nationality was, but I loved the dark skin around her clit and anus. Her ass was round and firm.

I ran my hand over her leg, hip and ass while looking at the boyfriend. "Fuck me," I said "You have this all to yourself?"

I squatted down and parted her pussy lips with my fingers. The brown hair opened like a zipper. It was the thin wispy stuff you have when you're only 20. The flesh inside was almost a pearl color and her pussy lips weren't swollen at all. I pulled back the dark skin of her clit and exposed its bright pink pearl. She had a good scent. I wanted to taste her youth.

I parted her lips again with my fingers and licked her opening, she jumped. "I thought you were just going to fuck me," she said, squirming a bit.

"Would you like me to stop?" I asked, licking her again very sensually.

"You can do that if you want," she said.

I pulled her cheeks apart and gently licked her anus, then her pussy lips and finally her clit. I did it as erotically as possible while peeking over her ass to see if the boyfriend was paying attention. He was rubbing his cock thru his pants.

I continued to enjoy her ass and pussy when I heard her moan for the first time. She put the phone down and adjusted her stance so my tongue could get further inside her. The deeper my tongue went the stronger her taste and scent was and eventually it filled the room.

I started gently rubbing her clit with my thumb as I licked both her openings. Her knees buckled a bit when my tongue darted in and out of her anus. She started to drip on the floor and her pussy lips swelled. I stood up, unbuckled my belt, and undid my pants while I caressed her ass with my other hand. She was ready for my cock.

I was almost fully erect from the pure enjoyment of licking her young pussy. I slid my hard cock between her thighs and rubbed it on her opening. Her boyfriend had his cock out now and was stroking it as he watched me prepare to fuck his lady.

I pushed her hips down so my cock lined up with her perfectly. I used my hand to rub my cock up and down her opening so her lips would part enough to let me in. She bounced a little in anticipation of my cock penetrating her. Once I had the head in, I held her shoulders and slowly pressed all 9 inches of me inside her. She rose up on her tiptoes when the last inch entered her.

"Holy Fuck you're big," she said in a breathy voice as I held all of me inside her, giving her body time to adjust to the fullness of my cock. I massaged her shoulders as I gently began thrusting inside her. Her young pussy was still very tight, and it squeezed me firmly as I gently slid in and out.