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.
