We had been working together for a few weeks before it started. I was new to the job and she was friendly. That's how it all begins.
We worked at as waiters in a local restaurant. It's a college town so there were plenty of young, attractive women waitressing and bartending to pay for school. Where we worked was full of them. They were all mostly party girls. They were the ones who would all go out after work and close down the bars. I'm not huge into bars, but that's not to say I didn't drink or didn't like to party. I have always been more of the small party type, into more intimate settings.
Sydney and I became quick friends. She was friendly to me when I started and I was friendly to everyone. Being single in a sea of attractive women was like working in heaven. After a few weeks of working together, I was being invited out after work for late night drinks, small house parties and just to grab some food.
Sydney was always there and we started to bond quickly. She was shorter than me, standing about 5'3 and had short brown hair which only hung down to her neck. Her big brown eyes and warm smile completed her kind and almost innocent look. When we went out after work it was usually after a quick shower and we didn't try that hard to dress up for each other. The nights were filled with undershirts and sometimes just sweats.
After a few weeks of group activities, Sydney and I began going out after work alone. Some nights it was because the others weren't up for it and quickly it became where they weren't invited. I started bringing Sydney around my friends more often. They almost all women and were small group drinkers too. We were an over sexualized group. A few of us and fooled around and we were all close. We frequently cracked dirty jokes and played games to see if we could get each other turned on.
Sydney thought it was great. She joined in on our games and jokes right out of the gate and I couldn't have been more pleased. I was surprised though at how quickly it happened. She had a boyfriend of 3 years and didn't seem to show it one bit when she was with us.
I was talking to her one night after work and she began to tell me about him. He was a few years older than her and how they had been together for some time. As of lately though, things have been in a slump. He was being distant yet somewhat controlling and the nights that she got to spend with me and my friends seemed like the only nights that she could let loose. After our chat I invited her to what my friends and I were calling pizza and porn night.
It was Cassie and Emily's idea and Sydney surprised me again by excitedly agreeing. We met at my place Friday night after work. I had just gotten home and finished showering when Sydney arrived. I invited her in and showed her around. It was shortly after that Cassie and Emily arrived with their movies and some vodka.
"We're skipping the pizza and drinking" Emily said with a big smile as she handed me the bottle.
I looked at Sydney who also had a big smile and I got to work mixing drinks as the girls put in the movie and made themselves at home. I brought the drinks in and took a seat on the couch between Sydney and Cassie. The movie was started and we started drinking. By the first sex scene we had slammed our first round and I got up to mix another. After a few more drinks, we were all starting to get pretty tipsy. Sydney cut herself off so she could drive home but the rest of us kept on. We watched the movie mocking the girls and their painfully obvious fake tits. We kept joking and asking each other if the scene did it for us or what we were into. Cassie would occasionally grab my dick over my pants and check to see if I was hard watching the movie. Every time she did, Sydney would look over and smile. The movie didn't turn me on but Cassie's hand on my cock was starting to give me a little wood. Before I knew it, Sydney said she had to get back to her boyfriend and left, thanking us for the night. Emily too said she was tired and was going to head back to her place, just up the street.
Cassie stayed, as she had a few times before. We never dated but over the course of our friendship, we had messed around from time to time. We were the best of friends with benefits. We even laid down some ground rules over it. So from time to time when we needed a little relief, we felt that it was our friendly duty to help one another. Tonight was looking like one of those nights.
After they left, I got Cassie another drink. When I got back from the kitchen, she had taken her shirt off and had the movie on one of the earlier sex scenes.
"You don't mind if I watch this one again do you? I think the girl is pretty hot and it's the only one I really liked."
"I don't mind at all" I said. "Is there anything I can do for you? Feeling a little wound up?"
"Will you rub my shoulders?" she asked as she slid off the couch and on to the floor in front of it.
I took my place behind her and started rubbing her neck and shoulders. Her eyes stayed on the girl on the screen as she got fucked by the landlord that she owed money to. Cassie let out a little moan as I found the knot in her shoulder that she wanted me to work on. She took another long drink and set her glass off to the side. As her hand came back from the glass, it found its way to her tits and began massaging them as she started to moan a little more.
I kept working on her shoulders and she kept working on her tits. Soon she started moving a hand down and started to rub her thigh. It didn't take long before her hand moved up and slid down into her shorts. She started to rub her pussy while she watched the girl in the porn start taking the landlord's cock in her ass. Cassie's moans started to get louder as I kept one hand working on her shoulder and reaching the other to work her tits. She stood up and slid her shorts down before sitting back on the couch. She laid back and spread her legs giving her hand more room to work and giving me a clear view of her neatly shaved pussy.
