A Regular Guy and His Hooker

CHAPTER 1

I am, in just about every way, a "regular guy." When this MOSTLY true story began, I was 55 and had just gotten divorced. I'd been working as a professional photographer, specializing in adult-oriented images and video. A perfectly loyal husband I was not. I really did not plan, or even want to stray, but after 6 years of a nearly sexless marriage, my needs over came all else.

At the time, I had been in several 3-somes with a married couple I knew who lived about 50 miles from me. I had also become a bit of a partier. I had become friends with a lot of people that also lived near that couple. One of these friends was an ex-biker, and one of the nicest people I knew. He always had LOTS of pretty, young and horny women at his house. It was known as the "Hang-Out." One afternoon, I dropped by the Hang-Out and my friend told me he'd bought a new digital camera, but was not getting good pictures with it and asked me to show him how to use it. After checking the settings and putting them to the easiest auto mode, I told him I needed to test it to be sure I had it right for him.

A young lady that I'd seen there several times, but never been introduced to, had been in the room while I was looking at the camera. As far as I knew, she was my buddy's girlfriend. When I asked him if anyone there would be a willing test model for me, the young lady said she would and before I had a chance to say anything, she was whipping her t-shirt off showing me her braless tits! Since that kind of thing was nothing unusual at the Hang-Out, I just pointed the camera at her and fired off 3 photos.

After reviewing them, I handed the camera back and told him not to change the settings and he'd be fine. He then wandered off, leaving me and the young lady alone.

We started talking about general stuff, nothing too exciting. She was a very cool lady to talk to and I regretted not doing so when I first saw her there a few months prior. After about 20 minutes, I felt like heading back home, a drive that usually took me 45 minutes or so. I told the young lady I was going to head home and where I lived. She asked me what I had going on at home that night, and I told her "nothing" but I just wanted to head back, and that my normal routine was to watch TV or file photos or film.

She then kind of startled me by asking if I wanted some company! Since I thought she was my bud's girlfriend, I was a bit tongue-tied. I made some lame excuse to put her on hold for an answer, and went to find him. When I saw him, I told him what the young lady had asked me and that I certainly did not want to step on anybody's toes (so to speak). He then threw me my 2nd start of the night by telling me to "Go for it - she's lots of fun!" I said something like "are you sure? She's YOUR girl!"' He just kind of laughed and told me that wasn't the case at all, and again suggested I take her up on the offer. I went back and asked her how long it would taker her to get ready, and she just said "Let's go!"

I thought, "why not" and we took off. We were getting along VERY well to that point, almost like we'd known each other for a long time, and that continued all the way to my place. We were talking about our likes and dislikes VERY openly, which was something I was not used to.

The conversation rapidly turned to sex. She was extremely open, something else I had not experienced in a long time, after 20 years of married life. When I asked her what she did for a living, her reply was "I hook." She said it so very casually, that what she'd just told me didn't register. I just kept driving and the conversation continued to get hotter by the mile.

As we were talking she pulled a small vibrator from her purse, lifted up her very short dress (reveling that a bra was not the only thing she was NOT wearing that night), put both feet up on the dash of my truck and went to it!

"You don't mind if I do this, do you?" she asked. "Of course not!"

Then I started thinking..."Hooker?" NAH! Must be something else, or maybe she was just fucking with me. So to speak.

After no more than 5 minutes she started to really get into what she was doing with the vibrator. She was starting to moan and move around in her seat. I could hear the egg humming louder than the radio, so I turned it off. Then I could hear the egg making that squishing sound that ONLY comes from a VERY wet pussy! I thought she came 2 or 3 times, which had me HARD as hell. But, I was driving, so...

We got to my house about 10 minutes later. I gave her a quick tour, the last room being the master bedroom and bath. When I showed her the bath, she said she'd like to take a shower, and I said "SURE!" She had just pulled her dress off when she invited me to join her (which I thought was cute!) She slid my shorts off and took hold of my now even HARDER cock and gently rubbed it while I took my shirt off. I turned the water on and we partied a bit while it got hot.

We then turned our attention back to the running water that was now hot and steaming up the bathroom. We both were getting pretty steamed up too! She got into the shower with me right behind her. We got each other nice and wet, and washed each other's hair. I found that to be EXTREMELY sexy! While doing that, we were talking about what kinky things we'd each done in the shower. Other than jacking off, I didn't really have much to tell, but this young lady had a few things to fill me in on. She told me to lie down, and who was I to argue! Once I was on my back in the tub, hard-on pointing straight up, she stepped over me and squatted until she was about 1 foot above my mouth. "Are you ready?" she asked. But I never got the chance to answer as her pussy made contact with my mouth and she came almost instantly.

Maybe a minute later it was over and I stood back up. We took turns washing each other slowly...VERY slowly! We played in the hot water spray until it started turning cold, so we exited and dried off. She asked what I thought about the little pee game. I told her" I loved it!" Then her "free" comment came back to me, so I asked her what she meant by that. "I told you that I HOOK, remember?" Just like in those old TV commercials, the light bulb went on, and there must have been a telling look on my face because she then told me "Tonight's my night off so don't worry!"

I had never paid anyone for sex and at that time, had the opinion that it was not a cool thing to do. That said, I had dated 2 women in the past that WERE hookers. One was an "escort" and the other a nude dancer, so I had no issue with what they did but I never paid them. Nor did they ever ask. THAT part of my realization wasn't a issue for me, but I think that I was simply shocked as I never suspected she hooked, even though she'd told me that very directly! She must have thought that I was turned-off by this as she started saying that if I wanted to just take her back home it was fine, but I put her at ease right away. "It does not bother me at ALL!" I told her. "I know you told me on the way out here, but it just went right over my head. I'm just surprised, that's all, and I was not concerned about you charging me either, as I'm sure if that was your intent, you would have discussed it with me before ever getting in my truck, right?" She still didn't look relaxed, so I asked her to tell me about one of her kinkiest encounters with her clients. "I love reading and being told wild sex stories!"

CHAPTER 1, Part 2

I have no idea how she decided which adventure to tell me about, but I DO remember she made a GREAT choice! We were laying on my bed and I was lightly tickling her hard nipples, with an occasional pinch thrown in, while she narrated one of her adventures.

"This happened when I was taking a bus home one night. It was kind of late and there weren't many people on the bus, maybe 5 others and they were all sitting towards the front." she related to me. "I sat all the way in the back by myself. 2 or 3 stops after I got on, a young guy, maybe 20 years old, got on the bus and walked to the back. He sat opposite of me. He smiled at me and struck up a generic conversation. He seemed a bit shy, so I couldn't resist teasing him a bit! I was wearing a very short, tight purple dress with fishnet stockings and no panties. I turned slightly towards him so we could talk without my neck being strained, or so I hoped it appeared!" As she was telling me this story, I heard her voice get more and more sultry.

She was definitely relaxing! We were now laying side-by-side on my bed, still naked after the shower as she narrated from an obviously horny memory!

"I started crossing and uncrossing my legs, while looking directly into this good-looking young man's eyes. HIS eyes, however, had changed into an almost constant star at my legs while trying to get a glimpse between them. We'd been talking about general things but then I asked if he had a girlfriend, which seemed to take him by surprise and he stumbled a bit before he said "yes." Then I floored him by asking if he thought she'd get mad if she found out I gave him a blow-job right here, right now! His face went blank, but his hard dick began poking out from the leg of his tight shorts! Instead of answering, he moved across to my side of the bus and pulled his shorts down to his knees, freeing his hard 7-inch cock!" By this time MY dick had gone hard again, almost painfully so! She had begun playing with her smooth-shaved pussy and clit as she spoke, her voice getting just a bit raspy by then.

"It was twice as exciting for me, as not only was I giving this guy I'd just met on a city bus a blow-job ON the bus with other passengers on board, but this guy was YOUNG, too! He'd told me he was 19 while we were just talking. I knew from the sounds and movements he was making that he was not going to last, but just when I thought he was getting ready to fill my hungry mouth with his cum, he suddenly pulled away, yanked his pants up and walked away, saying back over his shoulder "This is my stop!" And just like that he was gone."

"Not the ending I was expecting," I told my hooker! "It wasn't what I was expecting either!" she said.

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Chapter 3

Nosing around a local thrift store one day, and I came across something that caught my eye: A plug-in electric massager! I tested it and it worked just fine so I bought it. For $5! It had one of those 4-fingered tips on it, and I figured it would be good for my legs, as I had gotten back into riding my bike several times a week, and sore legs was kind of the norm after each ride. Well, I of course also tried using it on my cock, but it was too intense for me.

But, as you can imagine, the next time my hooker was spending the night, I showed it to her, but she was skeptical. Until she turned it on, that is! Nick-named "Big Blue" she tried it on her pussy, that was all she wrote! It took her about 15 minutes but she was in another world all that time and when she finally came, I thought she'd passed out! "What have I done?" I thought to myself..."I can never COMPARE TO Big Blue. I think I've hired my own assassin!" And unfortunately, she was done for that night, but it was FUN watching her!

About 2 months later, I came across yet another type of "massager" at a different thrift store. This was the type with a big disc on the end and it was even more powerful than Big Blue, so I spent yet another $5, knowing that I'd be doing more watching on sleep-overs!

That night, my hooker came by for another over-nighter. This time I tried something different.

I gave her the new toy and I took another crack at Big Blue. I'd had masturbation sessions face-to-face before, which was REALLY cool, but this was the first try with both of us using toys rather than just our hands and fingers. Man, oh MAN was this intense! I'd found Big Blue much more effective for me using some high quality lotion, and she seemed to be enjoying the new toy even more than she did Big Blue!

One thing that we'd learned about each other is that we BOTH loved watching the opposite sex masturbate, her even more than me! She told me this was a first with both using toys for her as well, and I'm here to tell you that we BOTH were putting ourselves into La-La land! She brought herself close to cumming two or three times but just couldn't get over that peak. AS much as I was enjoying Big Blue on my hard cock and watching her pussy getting more soaked by the second with the new contraption, I didn't feel like I was getting close.

All of a sudden her eyes rolled into the back of her head and she let out a sound I can't begin to describe! Her breath was getting more and more rapid and I knew she was going over the top! Then it happened! Not only did her pussy explode in a HUGE orgasm, I suddenly came at the same time...HARD! It was without any usual build-up, just POW! If it was not the most powerful cum I'd ever had, it had to have been VERY fucking close! It seemed to be much more intense that we both came at the same time! After I caught my breath, I tried to ask her if she thought hers was as intense as mine, but the next thing I knew, it was morning and her phone was ringing, waking us both up.

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Chapter 4

I woke to the alarm with a shudder...kind of in a fog (I'm sure you know the kind!) Next to me, my Hooker was out. Now, let me explain something at this point. This woman can SLEEP! I'm not talking sound sleep, closer to being in a coma! She had told me a couple of times in the past that if she conked-out before me, and I was not ready to stop fucking her yet, to just continue! I thought she was joking at first, but after the 3rd or 4th time, I knew she was serious. That said, doing something like that is a bit on the outside of my comfort zone. Until that moment, I didn't think I had much that WAS outside my comfort zone!

Well, getting back to the present, when I woke up to the alarm that morning, I was horny as hell. I looked to my left, and I instantly knew my Hooker was not yet anywhere near waking up. I however did not feel like jacking-off, so I thought, "WHY NOT?" Since she was lying on her side with that world-class ass pointing right at me,

I scooted up behind her with my hard cock resting right in her crack. She didn't budge or react at all. I pulled away a little bit, just enough to get my hand through the opening between her ass cheeks to reach her smooth-shaved pussy. It was obvious that she was NOT having any kind of groovy dream, but within only a few minutes, my fingers had done the trick and she was dripping. I pulled my fingers out and scooted back up, sinking my cock into her pussy with almost no effort. What was strange, no...WEIRD, was she didn't even flinch! (Good thing I have a very minimum ego!) I slowly started sliding in and out from behind her. She kept getting wetter, but ZERO body movement. I actually stopped at one point to make sure she was breathing!

That quick break was just enough for my brain to wake up a bit more and make me start feeling guilty for "taking advantage," despite the number of times she told me to go for it. It was just TOO out-there for me. Ok, that's a lie, but not by much! Then I noticed that I was feeling even harder than when I began this adventure, maybe 5-7 minutes prior. It took me very little time to get over my misplaced guilt and decided that if this didn't wake her up, I knew something that would, without question! But would that be going too far? I had to find out, so I slowly pulled my cock from her hot pussy (not all that easy to do, mind you) I slid down to where my face was lined up with her ass, used both hands to pull her cheeks apart and let my tongue start to attack her back door. I LOVE rimming her, and kept at it longer that I likely needed to get her anus ready.

I finally pulled my head out (get it?) and slid back up. My cock was aligned in no time so I pushed forward. The instant the tip of my cock made contact with her hole I almost came! But I managed not to and pushed in just a little, because I KNEW this was going to wake her any moment and she'd toss me off the bed while screaming at me to get the fuck out (it was my house but anyway...) no reaction. She didn't move at all. HHHmmm...I pushed in a bit more, but still nothing.

This went on until I was in all the way. She gave no sign of waking, or even being aware of having a hard dick in her ass on an unconscious level. So I started fucking her nice and slow, sliding my cock almost all the way out of her amazingly tight ass hole, then just before I was too far out, I reversed and pushed back in. All the way in. I stopped as I KNEW this would wake her. Nope...still out cold! At that point I really didn't give a fuck if I woke her or not. So I just kept fucking her ass.

I knew I wasn't going to last very long as knowing she was sleeping through it made it even hotter! This kind of surprised me, as I really did start this feeling kind of like a creep! I was only able to last about 4 or 5 minutes before I exploded a load of cum into her anal canal. It felt like I was pumping her full of every bodily fluid I had! When it was over, I just laid there behind her, trying to catch my breath, listening to her softly snoring. Like I said earlier, it's a good thing I don't have a fragile ego!

When we woke up the next morning, she asked if I'd been playing with her while she was asleep, so I thought, OK, she WAS awake - just faking sleep! So I said, "No, why?" She said "Because I have cum dripping out of my ass!" Turned out she WAS sleeping and I was busted! I knew she was pissed-off and was ready to endure her wrath. Then she started laughing and said "SEE? I told you I can sleep through ANYTHING!" Point taken!

Chapter 5

I got a call one day from a friend that lived in Arizona. He was selling the king size bed in his guest room CHEAP and he knew I'd been looking for one. This one has been used maybe 3 times and was like brand new. The price he would sell it to me for was a great deal even factoring in the gas and food for me to drive all the way there (about a 10 hour drive each way) I called my hooker and asked if she wanted to get away for 2-3 days. 4 hours later, my trailer, my hooker and I were on the road to AZ!

We left about 10 PM which made it dark for all but the last 2 hours of the drive. We were getting high and she was playing with my dick for a good part of the drive. We made a short stop at an exit that I usually hit for a quick piss and leg stretch. It really went nowhere and I'd never seen another vehicle there. Because of how it was laid-out, we could park there and play around a bit, being able to see any car coming from either direction in plenty of time to get our pants back up.

As I took the exit we were already ramping up for a quick fuck! But there was a surprise waiting...there was an SUV with a trailer that had ATVs in it sitting there pointing toward us. No lights, just sitting there. I had to go past it to turn around because of my trailer and when I passed it, I saw the US Border Patrol logo on the door! I really had no choice but to turn around as planned and when we drove past it again we saw there were 2 cops in it. Getting back on the freeway would NOT have been a good idea, so I just pulled over to the side, parked and we got out and stretched our legs. We were both nervous, but simply ignored the SUV and did what anyone taking a break from driving would do. Suddenly, they blipped their siren! Still no lights on inside or out of the SUV so we just ignored them. I figured they wanted to see if we spooked or not. We made a couple of sandwiches, had some water, I checked the oil, etc, then climbed back in and departed! It was at least 10 miles down the freeway before my hooker pulled my pants down and started giving me head, with me carefully watching my mirrors!