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Second job, Chapter 1

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Second Job, Chapter 1

After graduating high school in 1995, I decided to attend a two year tech school. The whole idea of a four year college, buried amongst other wary kids, and paying too much tuition never really did appeal to me. I had always been a tinkerer of sorts so I decided to be a motorcycle mechanic. Bikes were my passion so the attraction was obvious. So, off to school I went. Two years later I came out all primed up, excited to get into the industry and ready to grab the world by the tail. I found a job nearly right away with a local dealership with a long, solid history. It was a small organization but tidy. It was a commission job and that first summer went great. I figured life was going to be a breeze but it held oh so much in store for me. As autumn descended upon us and the bike traffic slowed dramatically, it became obvious I was going to have to manage my spending quite closely. I bounced my way through the first winter and coasted into spring on fumes. I?ve heard the phrase ?check to check living' but this was even tighter than that.

The summer of 1998 wasn?t as busy as most for the shop. There was of course our core business but the extra frills seemed to be few and far between back in the shop. We mechanics kind of considered the ?gravy? jobs like accessory installs our meal ticket but that kind of business just wasn?t there that year. I went into a panic of sorts, always thinking ahead on how I was going to make it through the ever approaching winter without starving. To top it all off, my room mate Mark and I were not aware at the time that we didn?t have to party like the end of the world was coming. We were both in our early twenties at that time and let me tell you, the part scene was smoking. Mark was a great friend and I was lucky to have him as a room mate. He was clean, courteous, and we generally shared the same interests. At the time, he was putting himself through school by working full time. He was going to school full time as well so it?s a wonder we found the time to chase girls and party like we did. Mark was well aware of my financial woes as we talked about it often. In fact there were several times he had to help me out. Mark had several short term jobs but finally landed an excellent paying position working at an adult book store. I constantly teased him about it but he defended it with everything. It paid through the nose for a college gig and it was actually a pretty nice place. I had been in there a few times to talk to Mark about one thing or another and the place really did impress me. It was laid out in such a fashion that patrons in the front end didn?t have to have the porn or the jack off booths near them. The front was all novelty clothing and trinkets. Mark?s job at the store is how this all got going.

Winter had come and as predicted, I was once again in a tough spot. Mark loaned me a few bucks to get me through the month of November. One week night (obviously there were no parties going on) we were lounging in the apartment and having a few beers when Mark piped up. He said, ?you know, I know a way you could make some weekend money.? I told him I was all ears. He went on to explain that behind the counter at the book store, they kept a list of phone numbers. By each number was a short nick name. This list labeled the stud list. When they would get calls from women or a group of women looking for male entertainment, they were referred to this list of phone numbers. He said, ironically, they did not provide numbers of women when men would call because they had been accused at one time of soliciting prostitution so it was dropped. (it still seems like a bit of a double standard to me but that?s the truth of it) Anyway, Mark was suggesting that he add our number to the list. I erupted immediately into laughter but as I calmed down I could see he was as serious as could be. He suggested that it would be a great way to ease my strains and that it could be very lucrative if done right. We ended the conversation by me telling him that I would think it over.

Over the next few weeks, as my borrowed money dwindled, I gave his offer some serious consideration. I had never fancied myself as a prostitute but I also never fancied myself as flat ass broke either. After struggling for quite some time over the issue, I finally resolved to go ahead with it but there was going to be some boundaries. Mark was always polite when we talked about it and I was relieved to say the least. He knew I was in a tough spot and he was a true friend not to put too much judgment on me. So, with the green light, he went ahead and added me to the list at the store. Of course, I had drank with all the people he worked with at one time or another so they pretty much all knew me. He had coached them extensively on my guidelines some of which were:

1. No parties. I didn?t want to be jumping out of cakes or whipping the bride to be. I knew this would drastically narrow down the field but this was on thing I did not want to be a part of. I wanted to keep things one on one and that was it.

2. No drugs. I didn?t mind if we loosened up with a few drinks or even a hit of weed but I wasn?t into dope. If the gal called and was doped up, take me out of the pool was the instruction.

3. Condoms were a must. No explanation necessary.

That was pretty much the short list I gave him. I caught some shit from the other kids he worked with right away but I think they all generally knew my situation. Mark had informed me that this was mostly a weekend thing. It wasn?t very often they got a call during the week. So, off I was to wait by the phone.

The first weekend I was on the list, no calls came. I sat nervously all weekend watching movies and wondering about my fate. I went to work on Monday feeling awfully strange. I wondered if the next weekend would be the one. It was all I thought about. My money issues were hanging all around me but I never gave them a single thought. To be honest, in those first days, I did actually lose sleep. The expectations were just so vague.

On Wednesday evening of the first week, the phone rang. Mark was working so I was alone in the apartment. On the other end, I heard a female voice ask for Jaeger (my nickname, I love the Stones!). I responded that this was the guy. Surprisingly, the conversation went very well. I could tell right away that she was very nervous and I could also tell she was not under the influence of anything. She introduced herself as Debbie, told me she was in her late forties, and gave me a run down of what she was looking for. We shared a couple shallow laughs and made plans for the following night. Shit was I NERVOUS! Every negative scenario went through my mind that day. All the way from not being able to get a hard on to an angry spouse walking in and mowing me down with a machine gun. It was hell. As the evening approached, I could feel myself starting to get cold feet. I called Mark and he tried his best to put me at ease. He told me there was no binding contract here and either party could bail out at any moment. I was not being paid for sex but for companionship. I was certainly more comfortable after talking with him but still nervous.

I had never been one to fret over my appearance too much. I always thought I was a decent looking guy and judging from my girl skills in the past, I was never too self conscious about it. But this was a different deal all together. She was paying for me to look good and I was petrified of not delivering. Quite a bit of extra care went into my appearance that evening. I wore tan dress slacks with a dark blue sport coat. I figured that was about as good as it was going to get so I ran with it. Before walking out the door, I sipped down two whiskey waters on ice to cool my nerves. As the drive across town dwindled to within a few blocks, I could feel my heart racing. I figured, this is it. In all of my swelter, I had failed to notice my surroundings. As the gap closed between where I was and her house, I did finally notice the elegant and oversized houses I was driving by. I allowed myself a quick drift away and wondered what kinds of jobs all these people had to live in these kinds of pads. Back to the task at hand as I noticed her house number neatly displayed in yellow against a mountain of brick. Debbie?s house had an all brick front with a large overhang over the front doors which looked like they stood twenty feet high. Actually, they were probably only about nine or ten feet high but it reminded of some kind of fairy tale castle. The house was a two story with large dormer windows that protruded from the second floor. I remember wondering why anyone would need a house that big. Something strange happened as I shut the car off and composed myself. All of a sudden I could feel what seemed like a truck load of confidence pour into me. I quickly reasoned that I was probably the youngest, best looking, classiest guy on that list at the book store so Debbie should feel lucky to have me. I knew it was some kind of self medicating pep talk but I figured it was working so I wasn?t questioning it.

I walked up the drive still admiring this freaking house when the door opened before I reached it and a pretty face appeared. A wide smile on a woman?s face greeted me as I returned the smile and we exchanged hellos. Debbie quickly gave my ego a boost by saying she was quite surprised by how good looking I was. She let it slip that she expected a tattooed ex junkie. I brushed it off with all my ?class? and gave her another casual smile. She invited me into the castle for a drink and told me she had prepared dinner for the two of us. As she led me into a kitchen larger than my entire apartment I took the opportunity to check out her figure. I was quite impressed to say the least. Debbie stood about five foot four inches tall, probably weighed about 130 lbs I guessed, had a fairly large breasts and a smoking ass. But by far her greatest physical feature was the combination of her hair and eyes. She had red hair and green eyes. They were intoxicating. Her skin was fair to accent that head of hair. She was quite beautiful to be honest. I quickly wondered what a woman like her would have to call a guy like me for. I had an expectation of servicing morbidly obese women who couldn't get a date if they advertised for one in the paper. But this was not the case in the least. Debbie could have walked to the nearest bar and walked home a half hour later with fifty men at her heals and the bar owner too. It confused me. So, to break the ice, I slowly probed into that issue. After commenting her on her looks so there was the mutual attraction was known, I very tactfully asked her why she called the stud list. She replied that she needed this sense of anonymity. Debbie said that if she paid for something, she felt she had more control since discretion seemed to be the most important part of this too her. If she had brought someone home from the bar, she felt they might get the sense that there was the possibility of a relationship and start contacting her when they shouldn't be. Actually, it was a damn good explanation. I could see exactly where she was coming from.

Debbie and I talked a bit about our personal lives. I was open and honest with her about my financial situation and told her that was how I ended up in this line of work. I also let her know this was my first gig. I could tell on her end there was a huge sense of relief once she found out I wasn't a professional gigolo. She told me this was her first time doing something like this and to be with someone in the same shoes seemed to set her at ease. I couldn't help but notice while we talked that her green eyes would flash with excitement when she smiled. We ate slowly while we talked and sipped wine. Debbie's fair skin cheeks were becoming more and more red with each passing minute. She mentioned that she had two grown children and a husband. Her husband owned a computer hardware importing business and was in the industry early on. The size of their house suddenly had an explanation in my own mind. She said he was a great husband and father but she stated without reservation that there was a huge hole in their relationship and that was intimacy. We were talking to each other over a granite covered island in the kitchen that had bar stool style chairs. I slid off mine and slowly moved around closer to her. I told her there was something I needed to get out of the way to make things less awkward. I took Deb a bit surprise I think when I leaned in and stole a kiss from her. I heard a bit of her breath escape along with a tiny moan. Not wanting to come on to quick, I started to retreat when she leaned in faster, put a hand on either side of my face and gave me back one of the most romantic and passionate kisses I have ever had. I could tell that both her body and mind were behind it and she was fully engulfed. That kiss never really broke and before too long I could feel her hand on my stomach and slowly working her way south. She moved down further and stroked the outline of my cock through my dress pants. Up until now, I was quite unaware that I was hard but it was not going unnoticed by her. The more she rubbed my cock, the harder her breathing became and the more she seemed to slither. Her lips left mine as she continued to move her kisses down my neck and chest. I gently held one of her breasts in my hand and the small of her back in the other. All of a sudden she broke away and nearly yelled out like a drill sergeant, 'I want to suck your cock right now but I don't want to do it in my kitchen!' Not knowing what else to do I let out an audible chuckle. She turned around and started walking out of the kitchen to which I followed. After we reached the west wing of the mansion (sense the cynicism?), we went up a long, curved staircase that led to the upstairs. As she entered through one of the doors, she turned around and said, 'we are all on the same page about being discrete right?' I replied that we were indeed. 'And we're both clean and no bugs of any kind right?' I replied again that was the truth. She walked up to me and began to kiss me once more. This kiss was fantastic but short lived. Debbie unzipped my dress pants and fished a hand inside the zipper hole. When her hand gently squeezed my cock, she closed her eyes and let out a large sigh. She sunk to her knees in the plush carpet, pulled my pants completely off me and began to suck my cock like the end of the earth was coming. She was moaning constantly and breathing like she was running a marathon. I was concentrating quite hard on my financial situation to ward off cumming too quickly. I thought about maybe getting into a different line of work all together. This bike mechanic thing was getting to be a drag anyway. I thought about this new thing that everyone was booming about called the internet. Anything to keep my mind off of what was happening. When I decided that she'd had enough fun, I gently reached down and pulled her back up to me. I cupped her face in my hands and kissed her. God she was beautiful! She finished getting me naked by removing my shirt while we kissed. I held her hand and led her to the bed that looked like something out of a movie. Like everything else in this house, the bed was flipping huge. I thought to myself quickly, 'no wonder you never get laid, he can't find you in this thing.' I sat her down on the bed and started slowly to undress her. After her blouse was off, I unhooked her bra and gently slid it off her shoulders with my finger tips to which she shuddered. I was surprised that those large breasts held their shape nicely without a bit of sag. She had a bit of baby fat in her mid section but it added to her shape quite nicely. She lay back on the bed as I began to remove her pants. As I slowly pulled off her black lace panties, I noticed she was completely unshaven with a nice patch of red pubic hair covering her woman hood. She piped up, 'there is something you need to know!' I stopped doing what I was doing and told her to go ahead. Debbie replied, 'my husband has been unable to have sex for nine years due to a traumatic surgery so it has been that long since I have been with a man.' I was a bit dumb founded. Nine years! Jeez lady! I told her with a smile, 'Don't worry about it Deb. If you want me to stop doing what I'm doing at any time, just say so.' I then slid her further onto the bed so that her feet rested on it. I gently sucked and circled her nipples with my tongue as I made my way down to give her pussy a treat. As I closed the gap to her pussy I used an old porno trick I had learned and gently blew on her lips. She shuddered and shook. I took my time actually making contact with her lips taking this opportunity to study her anatomy a little. Her pussy was beautiful with full outer lips that were engorged and swollen. The red hair stood proudly out of the top like a flag on a ship. I noticed that she had a terrific smell. As odd as that sounds, the other women I had been with to this point all kind of smelled alike but Debbie had a soft musk smell that made my cock ache. I began to softly suck on her outer lips and dip my tongue into her wet wonderland. After teasing her for a few minutes, I used my fingers to pull her lips apart and gently start to tongue her inner folds and suck on her engorged clit. Deb was panting and moaning like no other woman I had ever been with. Her hands were constantly going from my head to the sheets where she would clench them and squeal as her climaxes took hold of her. Every thirty seconds or so, her thighs would squeeze my head quite drastically. I finally concluded she'd had enough oral and decided it was time for something better. My cock ached with anticipation and the precum covered the tip. I moved up her body to let her know I had to break the action to put my condom on. She so cleverly whispered in my ear that it had been nine years since a man came inside her as well and that is what she wanted. Without further thought, I decided to abandon rule number three. Deb instinctively spread her legs and I reached down to place my cock in the right spot. I found her entrance and smeared my precum around it. As the head of my cock slipped into her pussy, she let out an audible gasp and gripped my biceps tightly. I kissed her neck and held my cock still as her body adjusted. As I felt her tension ease, I slid more of my man hood inside her to which her body readily accepted. Within a minute, I was completely bottomed out. I again held still and tried to make things as passionate as I could. Her juices were really flowing and I could feel my balls were drenched. She involuntarily started to rotate her hips to stroke my cock. I matched her slow rocking and within thirty seconds she went into outer space with orgasm. I was thinking to myself that this was a pretty easy target but was proud none the less. After she came down from her trip, I held myself up off her and really started to stroke my cock. She was moaning loudly and if it weren't for the size of this house, I would have been nervous the neighbors could hear. Debbie started doing something at that point that no other woman had ever done with me. She started talking dirty. Very dirty. She started by telling me how good it felt to have a real live man inside her. She then said, 'I can feel the tip of your cock kissing my cervix,' moan, moan, 'God I can't wait to have your sperm inside me, fill my pussy with it, your balls are fucking huge. Do you like being inside me? Do you like fucking a woman that has paid for it? It turns me on that this is paid service, God I love it!' To be honest, it was a huge turn on but it was really trimming minutes off my longevity. It is tough to think about money issues when the woman underneath you is telling you how big the head of your cock is. I asked Debbie if she wanted to switch positions and she quickly gave me a no. She replied, 'I want your cum as deep as you can put it inside me.' I once again successfully pushed off the temptation to go all porno on her and to try to slow things down a little. We found a nice rhythm with each other so I tried to keep it. Deb was digging her heals into my ass cheeks for extra traction. I couldn't help but notice how all of my senses were being tugged at. The room smelled of thick sex. Debbie's was quite wet so there was a constant 'cock pounding pussy' slap along with our fuck pace. Obviously, this vocal woman was piercing my ears with her vulgarity and profane references to our encounter. And the sights, every time I looked down at my cock, I could see a white foam developing in my pubic hair which I knew was the product of her sex oils. With all this going on, it's a damn wonder I could hold out all. Soon I started to loose the nice pace we had as my body began to speed up our rhythm. When I felt I could no longer ignore what my sex organs desired, I hooked my arms behind her legs, put them as far forward as I could get away with and started to pound her pussy with reckless abandon. Again, her screams were so loud but I was in the throws of my own orgasm so I didn't give a damn. I announced I was cumming and she barely gave a reaction other than to keep screaming like she was being murdered. Shortly before I came, I noticed that my balls ached feverishly almost to a painful status. The first rope of my cum shot into Debbie with such force that I know she could feel it. The succeeding strings of my semen flooded her womb and she screamed how she could feel her insides being filled. My orgasm seemed exceedingly long as my balls emptied string by string inside this woman. A minute or so after the last drop dribbled out of the end of my cock into her vagina, I slowly backed out of her to see my dick completely coated with our juices with a mound of this foam between us. It was completely covering both of our groin areas. I also noticed her expensive sheets now needed to be washed as it looked like someone poured a quart of cream into the bed. She was now just breathing heavy and staring at the wall. I pulled all the way out and lay next to her recovering body. I wrapped my arm around her mid section and she turned her side and backed into me into a spooning position. Not a word was said but I didn't care. I had this feeling like she got all of what she paid for and then some.

For what I guessed to be thirty minutes or so, we both had drifted into a light sleep. When I awoke, our bodies were in the same position with my arm wrapped around her mid section. I propped my head up to run my eyes down Debbie's body once again. I thought to myself how my high school buddies wouldn't believe this story if I told them. Here was this ultra sexy, super rich red head that was twenty five years older than I was, laying in my arms after a hot sexy encounter. I noticed then that my cock was once again getting hard and finding its way into her crack. Since she was still sleeping and we hadn't discussed anal, I figured I had better play it safe. I broke our contact and slid myself down her body once more. I got her to roll onto her back all the while still sleeping and once again took my position between her legs to lap up the results of our escapade. Her outer lips now did droop now a little since they were not so engorged. At the base of her pussy was the now drying foam I had witnessed between us. And of course, out of the bottom of her slit was a large white puddle forming of a liquid that I knew was inside my own body not long ago. This was a new one for me but I ever so slowly dipped the tip of my tongue into the puddle and started to lick her outer folds once more. I spread my semen around her inner folds which she quickly responded too. Her first response was to giggle a bit and make a comment about running with young guns. I sucked her clit for a short time again to get the pump primed. I sat up and told her to roll over onto her knees which she quickly did. I easily entered her from behind while holding onto her hips for support. Again, a nice rhythm was found and the slapping sound resumed. I felt her reach between us and with her fingers feel where I was entering her body. Debbie was not so vocal this time but seemed more like she was trying to enjoy the time rather than scream at the top of her lungs. I got the idea to start the dirty talk. This was my second round and I knew I was far less likely to blow my wad early so I was willing to take a chance. In mid stride, I asked if she had ever had a cock in her ass. There was a few slaps of our bodies together before she replied but she let out a deep and devious laugh. Deb said, 'not for about twenty five years sweetie. My hubby was never into that but I did experiment a few times in college.' I asked if she wanted to try again and she quickly responded she would. With the green light, I started using my intellectual tools once again. I lubed up my right thumb with spit and while fucking her, slipped it into her anus. I basically just held it there until her ass had dilated and adjusted to it. After a few minutes of that, I withdrew my cock from her pussy and instructed her to retrieve a dildo and some lube. Debbie got off the bed and flashed me that hot mom smile of hers while retreating to her closet. She came back with a small, steel vibrator and a bottle of oily lube. I instructed her to get back onto her knees and to work the vibrator into a nice pace into her pussy. I took the lube and poured liberally over her ass hole and went back to working my fingers into her. This time I did stroke them so that her ass would get used to the feeling of something coming back in rather than just exiting. She had her head on the pillow side ways so I could see her face and she was wincing with erotic pleasure. I told her I was going to enter her and I began to slip my well oiled cock into her ass hole. WOW, she was tight! I slowly, but deliberately held pressure into her which her body slowly accepted. I did not bottom out but when I got about half of my cock in, I held still and told her to keep stroking the vibrator. Sure enough, within a couple minutes, I felt the asshole muscles in her body began to relax and give me permission to hit spots that had been untouched for a quarter of a century. Slowly I started a short stroke of a couple inches to get her acclimated to anal. After about three or four minutes of that I stepped up the pace once more to full fledge fucking of her ass. Debbie also once again resumed the loud screaming. I think she wanted to talk dirty but her mouth was full of moans and squeaks and screams. This went on at this pace for about ten minutes before she told me to get all the way inside and stay still. I did as told and could feel her working her vibrator as deep as her fingers could push it and without warning I felt all of her muscles contract and release about five times very intensely. All the while she was fairly quiet except for her breathing. As the last squeeze took place she let out a horribly loud scream. It was loud enough that I was damn near a bit worried. I kept my eyes on her face and the wincing slowly subsided and she withdrew the vibrator. She locked her eyes on me and said, 'Use me like a slut. Fuck my ass until you cum you fucking stud. I can't wait to tell all my girlfriends this shit, how I rented a stud with a giant cock that fucked me silly for hours.' Once again I was about bursting with pride. I got a good hold on her hips and began to stroke my cock into her ass at a blistering pace. It didn't last long and I was filling Debbie's asshole with my cream. The volume of my cum wasn't there this time like the first but it was intense nonetheless. When I was finished using her, I pulled my cock slowly out and gazed at her two holes, both freshly fucked and oozing my seed. Her fair skin was red where our bodies had been contacting each other and where my hands had grasped her. She stayed with her ass in the air for a bit before sliding forward so she was lying on her stomach on the bed. I lay beside her looking for some kind of response. After a bit, Deb rolled onto her side so that our eyes met. She said softly with what I thought was a tear in her eye, 'Thank you so much for this. I truly had one of the best times of my life.' Man, her saying that so sweetly darn near brought a tear to my eye but before it did, I leaned in and gently kissed her lips. I told her that it was time for me to get going.

After a quick shower and a gathering up my belongings, I had Deb lead me to the door. We kissed gently and she once again poured out the thank yous. I think she genuinely appreciated what I had done for her. Her whole attitude made me generally very happy. I gave her my last good bye and had my hand on the door when she blurted out, 'Wait! I didn't pay you!'. Jeez, I had totally spaced it out to be honest. She took off walking for the 'west wing' again and over her shoulder asked, 'how much do I owe you?' I felt like a total heel. I had no idea what to say. As stupid as this may sound, in all my conversations with Mark about this whole thing, I had never asked what to charge. To try to cover up my stupidity, I said, 'Whatever you think it was worth.' Debbie laughed out loud as she disappeared from sight. About a minute later she came back into the room with a white envelope. She handed it to me and told me to let her know if that was not enough. I told her I was sure it was plenty and put it into my coat pocket. After another round of short good byes, I headed home.

When I came into the apartment, it was approaching midnight and Mark was all wide eyed and smiles. He gave me some jabs and I told him it was a thousand times better than I could have ever expected. As odd as it sounded, I actually felt like I got something accomplished. I think maybe because it was something I was paid to do, I don't know. Mark asked how much I had charged which once again I felt like an ass. I had not even counted how much she paid me. I retrieved the envelope from my coat and brought it back to the living room. Inside was a yellow sticky note with the words, 'Worth every penny, thanks again' on it with a lipstick kiss print below it. Behind the sticky note was twenty, one hundred dollar bills. Deb had paid me two grand for a grand total of five hours. I was absolutely stunned. Mark was elated. I knew that not every woman could afford a rate like this so I was going to have to come up with some sort of rate in the future. It was enough to cover my December bills and pay Mark back as well. All of a sudden, I felt a heavy burden lifted from my shoulders.

As time went by, Deb and I became terrific friends. She generally had me over about once every six weeks or so depending on her husband's schedule. There were times when we would spend complete weekends together. Deb became more comfortable going out in public with me and our friendship blossomed. Of course she always had the emergency response to explain who I was if someone she knew asked. She was a faithful customer for about two years until her husband decided to move the headquarters for their enterprise further south looking for cheaper labor. It was a tearful goodbye for both her and I on the eve of her departure. It is hard to watch someone walk out of your life that you feel you know so well. I think about her often even now. I wonder what good things in life have found her. I hope it has been the best of things.

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