Expanding My Sex Life Ch. 01

I was 22 and had just taken my first job since I graduated college. I have a degree in administration so I applied at several places where I thought I could move up quickly. I had some money saved up from the job I had while in college, but I moved back to where I grew up and the job market was slow and I was quickly running out of money. I decided to start making repeat visits to the places where I had applied. I was having no luck until the next to last place I went. It was a small business that did shipping with only twenty employees. I got to talk to the owner and he took a look at my resume. He frowned and said that I was too qualified for the position he had open but he would keep me in mind. I told him I would take whatever he had explaining my money situation and that I just needed a job. This was a Thursday so he told me to start work on the next Monday.

I wanted to make a good impression so I took the money I had left and bought four more outfits to wear. I always enjoyed wearing short skirts with matching jackets. My mom always told me the skirts were too short, but I felt they were still professional looking and I turned a few heads as well. My best friend in High School had also moved back so we planned a quick getaway weekend with our boyfriends.

Amy has been my best friend since junior high and we were like sisters. Everybody called us Laurel and Hardy because I have always been thin and she has always been bigger. I'm five foot three barely one hundred pounds, Amy is five foot eight and two hundred pounds. We both have A cup titties even though she's a hundred pounds heavier than me, so I always joked mine were bigger because it looked like they were on my skinny body.

The four of us decided to go camping at a nearby lake and since all four of us were broke we brought my boyfriend Kent's tent. Kent and I had been off and on for nearly six years. He was a decent looking guy, five foot eight, hundred and fifty pounds or so with black hair and a pale complexion. Sex was good with him even though his cock was only six inches, it fit my pussy just right and he usually made me cum twice, once with his tongue and once with his cock.

Caleb was Amy's boyfriend and I never liked him. He was only five foot six about two hundred and fifty pounds and he looked like a troll. He was arrogant and thought very highly of himself. He did however have a cock that was eight inches long and as thick as a coke can. He was constantly hitting on me and even though he and Kent were also best friends, he was always making fun of how small his cock was. The four of us have had sex in front each other many times and Caleb always made sure that I saw his cock. This trip was no different as the four of had sex several times. Caleb had asked Amy numerous times about swapping partners to which she always replied no.

On the way home Amy told me she didn't really like the way Caleb acted but she did love him and he took care of her sexual needs. I told her that wasn't the most important thing, but she didn't think she could find anyone else because of her size.

I had been at my new job a couple months and really liked my boss. He was single, fifty years old and was in incredible shape. His hair was almost completely gray and he was close to six foot talk probably two hundred pounds. I was staying late one night finishing up some cleaning when he walked by the office I was in. He stopped and asked if I was nearly thru that he was trying to leave. I told him I was and that I was sorry that I held him up. He said no problem and that he appreciated how hard I had been working. He told me that he knew I needed more money but there wasn't anything available but he had another offer for me and we could talk about it tomorrow.

The next day he called me in his office and explained he lived alone and his housekeeper had just moved and he needed someone to clean for him. The job paid $75 dollars twice a week but if I wore a naughty maid outfit the price would go up to $100 and if I only wore a thong, thigh highs and high heels it would be $150. He told me to think about it and let him know and that he didn't want me to feel uncomfortable. I knew I could really use the extra money and the possibility of an extra $300 dollars a week was very enticing. I stopped by his office before I left for the day and told him I wanted the job and I would decide which attire that I would wear when I showed up. He told me that Monday and Thursday evenings after work would be the two days that I would need to clean.

I thought about it over the weekend and weighed my options. Did I want to parade around in nothing but a pair of thong panties in front of my boss, or did I want to bite my pride and make an extra $300 dollars a week. In the end money won the fight and I invested in a new pair of black thigh highs to match the black lace thong and black high heels that I already had.

Gary, which was my boss name, had ask me to not let the other employees know about me working for him on the side. I was nervous and excited thru out the day and couldn't wait for five o'clock. I followed Gary to his house which was huge. He showed me around explaining what he wanted and where all the cleaning items were. After giving me the tour he told me I was on my own and he was going for a swim. The main living area had huge windows that overlooked the swimming pool, hot tub and party pavilion. I had changed into my "work" uniform and even though I was pretty much naked I didn't feel as weird as I thought I would. That was until I started cleaning the living area and noticed that Gary was completely nude. He was tan line free and was in better shape than I envisioned him to be. He was just getting into the pool and all I could see was his ass but he was gorgeous. I didn't want him to catch me looking so I kept working, but after seeing his backside I was interested in what the front had to offer.

I was finishing in the master bathroom when Gary shocked me by walking in completely nude. My eyes immediately went to his cock. Now I have only seen two guys nude in my life and as I mentioned before one had six inches and the other had eight. Gary had eight inches and wasn't hard. I couldn't believe how thick and long his dick was, his balls were also huge along with being completely shaved to match his cock. He asked if I was thru that he needed a shower. I told him I was and that I would see him in the morning. I was so rattled by the sight of his naked body I was already in my car when I realized that I was still in my "work" attire.

It had been about three months since I had first seen the biggest cock in my life and my sex life had gotten crazy. With the extra money I was making I was able to move into a one bedroom apartment. To celebrate I invited Kent along with Caleb and Amy over for a party. After way too much liquor the four of us made our way into the bedroom and broke the apartment in with its first orgy. For some reason I couldn't take my eyes off of Caleb's eight incher as Amy sucked on it. I was doing the same to Kent when a thought crossed my mind. I knew Caleb wanted to fuck me and Kent had mentioned several times that he wondered what it would be like to fuck a big girl. The alcohol kept me from thinking clearly as I turned to Amy and asked her if she wanted to switch places. There was a moment of silence between the four of us until Caleb replied " Fuck Yeah".

Both of the guys laid beside each other on the bed as they put their rubbers on. I couldn't believe I was really going to do it as I climbed on top of Caleb the troll. He immediately grabbed my ass with both hands as I told him to calm and let me do the work. As I slid slowly down on his cock I never imagined how much my pussy was going to have to stretch to take him in, it felt like he was going to rip me apart. He tried to start working his cock but I made him stop. I was moaning louder than I ever had with Kent and was worried about hurting his feelings but Amy was fucking him like a crazy women and he was smiling like a mad man. Eventually I started fucking Caleb faster and grinding my pussy harder, he was sucking my tits swapping the left and right, all the time grabbing and squeezing my ass.

I guess my buzz was wearing off because the sight of Caleb's face was starting to get to me. I was however enjoying his cock so I decided to spin around and do reverse cowgirl on him. We stayed in that position for a few minutes while Kent had Amy on her back and was going hard and fast on her. I slid off of Caleb and told him I wanted it doggy style. I went down on my chest and stuck my ass up in the air. He shoved his cock in and I told him to fuck me hard. I started to fantasize about Gary fucking me and as much as I knew it was going to hurt, I told Caleb to fuck me harder, I told him I wanted him to pound my pussy. He grabbed me around the waist and started pulling me back on his cock as he was pumping me harder and harder.

I was screaming with extacy knowing I was fixing to cum I begged him to give it to me as hard as he could and to slap my ass. Caleb screamed he was fixing to blow and as big as his cock is, I swear it got bigger as he was cumming. I continued to grid my pussy on his cock until we both collapsed with exhaustion. I rolled over on my side facing where Kent and Amy was and to my surprise the two of them were looking at us. They both said thanks for the show as they began laughing. I was exhausted as the four of us laid there naked, giggling about what had just taken place. My pussy was sore but I did have the best orgasm I had ever had. That would be the first of many sexcapades for the four of us. Little did I know that the next sexual adventure would involve Gary and Amy.