I knew Emily had fucked Michael, her ex, while I was sitting in the next room. Emily knew I knew, yet we never talked about it. After we drove back to the city it was as if it never happened.
Emily was my girlfriend again, although I still never got to fuck her. She did let me go down on her often when we were alone. I had to admit her pussy had power over me. Emily was by far the most beautiful girl I had ever been with...one of the most beautiful girls I had ever seen. I felt lucky every time I got to touch her. Emily would just have to use one finger to signal me to come to her and I would quickly find myself on my knees, between her legs. Emily loved the way I worked my tongue on her and she would sometimes have me go down on her for over half an hour. I loved tasting her, loved knowing I was making her feel that good.
Sometimes Emily would let me jack off after I had made her cum. If i was lucky she would watch. When she did I would cum very quickly as I loved to jack off looking at her body. Sometimes she would tell me to take care of myself when I was alone. On these occasions I would often jack off when I was alone in the bathroom, or in my car on my way back home.
More and more though, when my girlfriend would leave me with my cock hard I would head over to her friend's place. Isabel was not especially attractive, and she carried a few extra pounds, but she had become a good friend and she gave an amazing blow job. More recently I had discovered the joy of fucking her huge tits. After being teased to the point of insanity by my girlfriend it felt so good to have my cock pushing between Isabel's sweaty tits, thrusting until I came all over her. Of course I would always go down on Isabel until she came, my face buried between her giant thighs.
I felt a little bad since I was cheating on Emily like this, even though Emily had made it pretty clear from the beginning she was fine with me enjoying her friend. She had in fact tricked me into fucking Isabel one night and another time she had Isabel give me a blow job. One thing was sure, my tongue was getting sore servicing both girls.
One evening I had just finished going down on Emily when she told me that Dan was in town and wanted us to take him out on the town. Dan was Michael's best friend from college. Like Michael, he was a lacrosse playing jock. I had met him a couple of times. As far as I knew Emily had never fucked Dan, but memories of watching Dan spank her, and her hand squeezing his cock popped into my brain. I looked up at Emily, trying to think of how to nicely advise that I didn't really like Dan or want to take him out.
"Aww, I knew you'd be a sweetie Ian." She kissed me on the forehead. "Dan wants to head out late. Pick me up at 11 then we'll swing by his hotel."
"Now you head on home, time for me to go to bed."
When I got to my car I drove up the block to a quiet area they started to jack off. I thought of Emily and how sexy she looked when she pulled up her skirt and allowed me to lick her, then I remembered how perfect her ass looked at a party when Dan bent her over Michael's lap and pulled down her panties for a birthday spanking. Guy after guy took turns smacking her ass and as Emily had squirmed so much she showed her asshole to everyone looking. I came into some tissues I kept in the car for this purpose, caught my breath and drove home.
When I got back to my place I was still concerned about Dan so I called Isabel. "Oh, careful of him." Isabel cautioned. "Dan always wanted Emily...well all the boys did, but Dan was used to getting what he wanted. Even though Emily was pretty easy in those days, he could never have her. Michael was the alpha on the lacrosse team and Dan was his best friend."
I didn't sleep well that night, feeling a sense of dread about having to bring Emily to a man I knew wanted her. A man who had known her from the days when she had been rather wild. I was also feeling very aroused, remembering all the times I had seen Emily looking so sexy. Times when she was alone with me, but also times she had been with her ex, with Dan. I jacked myself off two more times that night but still couldn't sleep.
The next day work seemed to go slowly. I left a little early to pick up Emily and she let me choose what outfit she should wear. They were both a little more revealing that I would have hoped for our dinner with Dan, but I chose the simple, short black dress I thought she looked classier in. I watched her change, and she winked at me, knowing how much I wanted her. I knew she prefers I don't touch her when she is doing something so I just watched gratefully. I noted she put on nice black panties I hadn't seen her wear before. I felt myself harden as I watched this beauty put on her dress, then helped her zip it up.
As I drove Emily to Dan's I admired her bare legs. Emily seemed quiet, as thought she was lost in deep thought.
Finally she spoke, "I don't want you to get jealous tonight." she said gently. "I know Dan can be a bit forward, but he is an old friend and he is a guest in our city."
I wasn't clear what she meant, but I nodded, ever eager to please her. She smiled and touched my leg. "That's my puppy." she cooed.
Dan had his hands all over my girlfriend almost as soon as we got to his hotel room. He gave her a kiss and a big hug as he lifted her off the ground while as squeezing her bum.
"There's my girl." he said brightly. "God you look hot."
He stood back and admired her, then directed her to turn for him so he could enjoy how tight her dress clung to her ass.
I tried to break the apparent tension by approaching him and he finally took notice.
"Hey, Ian, wow you've hung in a while eh sport?"
He almost crushed my much smaller hand when he shook it then offered us both beers. As we talked...well Dan and Emily did most of the talking, I remembered why I didn't like Dan. While Mike may have taken advantage of my girlfriend, even while I was there, he was always polite with me. When Dan paid me any mind at all, he made no pretense of politeness. I wondered again why Emily even wanted to bother with him.
"Let's head out!" he exclaimed, interrupting my thoughts. Ian you drive, Emily and I are going to go hard tonight."
I was concerned, as Emily could get wild when she drank, but before I could answer Dan was already shepherding Emily out the door and I followed. As we got to my car Dan opened the door gallantly for Emily, then as I got in the driver's seat he got in the backseat with her. I was confused at first but they were talking and didn't want to interrupt. I pulled out feeling quite like a chauffeur. As far as I could see Dan didn't do anything too aggressive. He had his hand on her leg as he told her about what he'd been up to but more in a friendly way from what I could see. I got more concerned when he took out a joint and the two of them started to smoke. I sensed Emily was ready for the kind of wild night Dan was excited to have and knew that might not be good for me.
By the time we got to the bar the two of them were giggling as they talked. Dan had his arm around my girlfriend as we walked in. He took Emily over to the bar and I followed behind. He ordered three beers and two shots then toasted seeing Emily and we all raised our beer bottles. After a drink Dan and Emily both downed their shots and cheered. Dan told me to find us a booth so we could sit down. I thought I saw an empty one on the other side of the bar and wandered over to check. They didn't see me when I waved them over and when I got back I saw Dan's hand was back on Emily's ass as they talked, their faces close together. I interrupted to tell them about the booth. I put my arm around Emily as we walked to it, but when we took our seats Dan sat beside her, leaving me across from them.
I sat and watched as they downed more shots and shared old memories. Emily was clearly feeling no pain and did not resist when Dan stroked her bare leg up and down or even when he kissed her on the lips. I protested when he kissed her but instead of apologizing Dan started telling me about how Emily used to be so wild that there were parties where she had made out with every boy there. This shut me up as I was somehow embarrassed for Emily. Frustratingly I felt myself harden as I imagined her at one of those college parties, guys lined up to make out with her.
I didn't trust Dan alone with her but I really had to pee so I finally excused myself. I tried to be fast and walked quickly back. I felt relieved when I saw there was two other guys at the booth with the two of them. Dan's hand was around Emily, but nothing bad was happening, the four of them were just talking.
