My First Time With A Hooker - Cover

My First Time With A Hooker

by Master Jonathan

Copyright© 2021 by Master Jonathan

Erotica Sex Story: In the big city for a job interview he is looking around at the sites when he sees a hooker looking for a customer. He decides to pick her up and take her back to his hotel for some fun...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Workplace   Oral Sex   Prostitution   Illustrated   .

My name is Mark Woods and the story I’m about to tell you is true. It happened about five years ago now ... I was twenty years old and fresh out of a two-year technical college with a brand new Associates Degree in Computer Sciences. I was in Philadelphia on a job interview – my professor told me of a new company opening up and put in a good word for me, so I was following up on it.

I wanted to get into the whole computer security field as my professor told me that was where the good money was and the field was rapidly expanding. “The more our society depends on electronics, the more we leave ourselves open to hackers and computer viruses and malware,” he said. And I seemed to have a knack for figuring out the problems and fixing them.

Anyway, I had just finished my initial interview and was just driving around Philly looking at the sites. I’d lived my whole life in Casper, Wyoming and I’d never been east of the Missippi River so seeing how they did things on the East Coast was exciting to me.

I needed to stay in Philly for a couple days because there was two or possibly three interviews I had to get through and then because this was computer security, there was a pretty extensive background check too.

I would be working for a company with ties to some major players in the computer world and they wanted to make sure I wasn’t some computer terrorist looking for a way in to cause mayhem. They also wanted to make sure I couldn’t be coerced into becoming one, either through blackmail or being bought off.

I understood their caution of course and had no problem taking a little “vacation” in the big city. After all this was the first time in my life that I didn’t have to worry about school or parents or anything like that. I was finally free! For a brief glorious period I wouldn’t have to answer to anyone! It was a very heady experience, let me tell you!

I was always the good kid – I never caused (too much) trouble for my parents, never got in trouble with the law, was good in school etc., etc. I grew up in a pretty conservative household so now to be “let out of the yard to play” was quite a big deal to me!

My last interview of the day had ended about 4:00 that afternoon and I decided to have a little look around before grabbing a bite to eat and going back to my hotel room I found what looked like a nice place, a small mom and pop family restaurant, and ate dinner. It was getting pretty dark by the time I turned the headlights of my rental car towards the hotel.

Not knowing much about Philly except what I’d seen on TV shows, I soon found myself in a section of town I probably shouldn’t have been in. I can’t say I was “streetwise” by any stretch but I did have a modicum of common sense and the hairs on the back of my neck were on high alert.

I began to notice there seemed to be an abundance of women out this evening, which at first was strange – ladies shouldn’t be out alone at this hour especially in this neighborhood. Then it hit me ... these weren’t “ladies” at all. They were prositutes!

I began to take more notice of them. There were all sorts of girls working the streets – short girls, tall girls, girls so skinny they could hide behind the street poles, and girls that could barely waddle down the street. Black, white, Asian – it was a vertitable banquet of prospective pussy!

I had to stop at a red light and I saw a very attractive lady of the evening working that particular corner. As I waited for the light to change, I watched her. Cars would drive by, the driver’s honking and whistling, and she would wave and shimmy her ass for them.

Suddenly, and for what reason I don’t know, she turned and we made eye contact. She smiled and walked over to my car. Being raised to be polite, I rolled down the passenger window thinking she wanted to talk to me.

“Hi baby, are you looking for a good time?”

I tried to act cool and not at all like the fresh-off-the-farm, small-town kid I really was. “Sure darlin’ I’m always up for a good time!”

I had never even seen a prostitute much less enjoyed their company. But this was the start of a new life, I was on my own for the first time ever and I had a wad of cash in my pocket looking to find a new home!

I unlocked the car door and the woman got in. She was even more attractive in the light of my car’s interior light. Not really sure what else to do at that moment I introduced myself.

“Hi, I’m Mark.”

“Nice to meet you Mark, My name’s Angel.”

“Angel, huh? Well, it fits you.” And it did – she was prettier than anything I’d seen back home in Casper!

“Aww, you’re sweet. So what kind of a party are we talking about? What would you like, honey?”

“Well, I’m not really sure. What do you do?”

“I’ll do anything you want, baby. It just depends on how nice you are to me.”

“Huh?”

“You’ve never done this before, have you sweetie?”

I looked down. “No, I haven’t. We don’t have girls like you back in Casper. No offense.”

“None taken. Well, honey, I’ll tell you what. Since you are new to this and you seem like a nice guy – sweet and respectful – I will give you the ‘working girl’s special’. For $100.00 I will fuck you and finish you off with a blow job. I’ll even let you cum in my mouth and on my face, just like the girls in the porn movies ... you HAVE seen porn movies, haven’t you?”

“I’ve seen video clips on the Internet.”

“Well, there you go. Just like the girls in those video clips then. Does that sound okay to you?”

“That sounds okay. But this car is pretty small ... where do we do this?”

“Where are you staying? I assume you don’t live here, right?”

“No, not yet. I am here for a job interview but for right now I’m at the Motel 6 on Roosevelt Blvd.”

“Oh yeah, I know the place. Okay honey, let’s go there then.”

I began driving us to my hotel room. Looking back on the whole thing, I can’t believe I was so naive and trusting, but living in a nice upscale neighborhood of Casper Wyoming is a long way from the inner city streets of Philadelphia. Where I was raised if we had two or more cars broken into it was considered a crime wave!

We got to the motel and I parked the car in my parking spot right in front of the room. My room was on the second floor so I let her go ahead of me and it turned out to be a smart move on my part. As I walked up the stairs behind her the very short denim skirt she wore gave me a wonderful view ... and letting me know that she was not wearing any panties either!

“Damn!”

“Like the view back there do you, baby?”

“I sure do! And I thought I’d seen most of the attractions in Philadelphia already. I’m glad I didn’t miss this one!”

She stopped and turned to look down at me. She smiled and blew me a kiss. When she started again she made sure to swish her hips a little more giving me a little pre-game show!

We got to the room and I unlocked the door, holding it open for Angel. She smiled and stroked my cheek as she walked past me into the room.

My hotel room was simple and utilitarian. There wasn’t much decor or luxury – I couldn’t afford the higher end hotel prices since I didn’t yet have a job and I had to pay for the trip to and from Philly besides the room. But it was clean, it had a bed, a TV, and WIFI, so it was enough for my needs.

Angel came into the room and promptly flopped down on one of the two queen-sized beds.

“Ahh...! This is gonna be fun – I don’t always get to play on a bed! Most of the time it’s in the back seat of a car or kneeling on the ground while I suck a guy off! You’re gonna spoil me, baby!”

I’m fairly sure she would have liked to lay on the bed a lot longer, but there was business to tend to. She sat up and scooted to the edge of the bed.

“I get the money first, honey. Sorry, but a girl has to be careful.”

I reached into my pants pocket and pulled out my wallet. I picked out two fifties and handed them to her putting my wallet back in my back pocket. Happy with her payment, she smiled and reached behind her neck to untie the knot holding up her halter top. She dropped the front of it down and I got a look at her very nice tits.

Now I’m no connoisseur of women. I’ve had my share of dates and girlfriends and I was no virgin, but unless it was blatantly obvious, I couldn’t tell real tits from fake ones. All I know is that this woman had a great looking set – not overly large, but well proportioned to the rest of her and big enough to be impressive. They had just a slight bit of natural droop to them and the nipples were fat and hard. They looked delicious and I so wanted to chew on them!

I guess the expression on my face telegraphed what was going through my mind. “You want to suck on them darling? My girls love to be kissed and licked and chewed on!”

I certainly didn’t need to be asked twice! I moved in on her luscious tits like I was starving and Pushed her backwards climbing on top of her and straddling my little coquette. She giggled at first but those giggles soon turned to moans as my hungry mouth fastened on her tit and I went to work. She found out that while I might be young and small town, but I was NOT inexperienced!

I licked and sucked on the meaty button as she pulled my head down on her tit more trying to stuff more of it in my mouth. My hand moved to her other tit to let it know I hadn’t forgotten about it. I rolled the little bud between my fingers lightly tugging on it and flicking it as she gasped.

She moved my mouth to her other tit after a few moments and I was all too happy to give it its share of attention too. But instead of playing with her now unoccupied tit, my hand instead moved down between her legs. I was pleased to find her already getting damp. I could also see the she was well trimmed and not overgrown. These were all good signs.

While I dined on Angels soft creamy titmeat, my fingers played in her pussy, toying with the lips, rubbing her little clit and circling the rim of her tunnel. I purposely didn’t go inside her, I wanted to save that for my now steel-hard cock. Besides hearing her whimper for it was turning me on even more!

“C’mon, baby, you paid for me, now use me! Please fuck me, you are making me crazy with your teasing! Fuck me! Give me that big fat cock!”

I knew that at least some of this talk was just ego boost for me – girls in her line of work always tell you that you are the best lover they’ve ever had and that you have a huge cock and all that stuff.

It’s all bullshit and everyone knows it, but it makes the guy feel like a real stud even if he isn’t. Still I would like to think that maybe a little of that talk was genuine – after all I was teasing her and making her wait while I built up the sexual tension and anticipation.

Her moaning and her whimpering did encourage me and fake or not, it gave me the confidence to start taking the lead in this union.

“Relax, darlin’ ... I paid for the experience, not by the hour. I’m gonna get my money’s worth!”

Angel moaned again, knowing now that this wasn’t going to be one of those “wham, bam, thank you, ma’am” kind of jobs. She was going to be here for a few minutes at least and in that time I wanted to make sure she had as much fun as I did!

After I’d played in her box for a bit and gotten her dripping wet it was time to see how that box felt around my cock. I got up and started to take off my pants. She watched as I undidn my belt and pants and pulled them down and off. When I went for my boxers she put her hand on my stopping me.

“Can I do that?”

I smiled and moved my hands away, letting her have her way. She smiled and at first she just felt my cock through my shorts pulling them tight to see the bulge my hard cock made in them she stroked the bulge and kissed it ... she could do her share of teasing as well! Then she took the waistband of my boxers in both hands, and pulled them down slowly until the tip of my cock appeared.

 
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