The Benefit of Friends

This is a work of fiction. The events in the following tale are figments of my imagination. All characters are REAL; however the names have been changed to protect the innocent. I encourage everyone to send comments, positive or negative, to me.

Prologue: Natalie

I guess it was mostly my fault. Maybe if I had not worked so much. Maybe if I had not been so tired. Maybe if I would have been more willing to make love like in the old days. Then maybe all this would not have happened.

My girlfriend, Natalie, and I met in college 7 years ago. At the time I was in a relationship that lasted much longer than it should have. Natalie and I both knew there was an attraction between the two of us, but neither of us acted on it. The attraction was not just physical. She and I had a mental connection that I did not have with my girlfriend at the time.

Although I lived near our college and Natalie returned to her home about an hour and a half away after graduation, we stayed in touch via text messages and cards and letters. When my relationship finally ended, and I was able to pursue other interests, Natalie was the first one I went after. Within five months I was packing my bags and moving into an apartment with Natalie in her town.

At first, our sex life was great. Before I moved up to be with Natalie, we would get together every week or so and rarely left the bed. Once we moved in together, things were mostly the same. Natalie and I would have sex several times a day.

Then things started to change. Like I said, maybe it was my fault. Maybe I became less sexually interested. But I never, ever, expected her to do this.

Natalie's mother got me job at her office when I moved in with Natalie. Occasionally the job required me to go on overnight trips. I was scheduled to go on one of these trips one month, but an unexpected issue arose at the offsite office, and the trip had to be canceled. I did not tell Natalie, and tried to surprise her by coming home unexpectedly. What I found when I came home is what started this wild and crazy adventure.

I never expected to find her in bed with him. I say "him" because to this day I still do not know what his name is. Frankly, I do not really care either. Sure I was mad at first, super mad. But, damn it, I love her. I have since that first day of college, and I probably always will. That is why, when I finally calmed down, I could not just leave. I knew there was a way for us to work it out. I got another huge surprise when Natalie told me her idea, though. At first I said no, there was no way I was going to go for it. But Natalie insisted that the only way I could ever forgive her, was if I too had sex with someone else.

She said she did not care who. She said she did not care when. She said she did not even want to know when or if I had done it. She said that she would assume we were even, and we could keep our relationship intact. I was blown away.

"Why stop there?" I asked, anger rising in my voice.

"What do you mean?" Natalie answered.

"Why just once? Why don't you keep fucking him or whoever and I'll fuck whoever I want and that's how it'll be?" I asked. I really did not mean it. It was really just the anger talking.

But when her answer was "Well that might be a good idea," I did not know what to say.

So here we are. Like I said, it is my fault. Hell it was even my idea. And now I have her blessing to sleep around with other women. Honestly, I never planned on actually doing it, but the more I thought about it, the more I started looking at other girls. And the more I started looking at other girls, the more sexually attracted to them I became.

How do I go about hooking up with someone else though? I was new to this town and did not know anyone other than Natalie's friends and family, and clearly I could not approach any of them for help. Like I said, I was not even 100% sure I wanted to do anything, but little did I know just how far I would go.

Chapter One: Allison

I was searching the internet one day when I stumbled onto one of those adult dating sites. I had nothing to lose, so I created an account just to see what would happen. A few days went by and I got no action on my profile. I realized it was a long shot anyway.

Natalie told me she was going out with her friends one night. Deep down I assumed she was with him, or some other guy. I did not really know what I was doing, or what I was expecting, but I went to a local bar for some drinks. I knew this was a popular hangout for most of the 20-somethings in town, and thought maybe I would meet someone of my own.

After being there for half an hour I was ready to leave. I was having absolutely no luck with any of the girls in the place. Just then I felt my phone vibrate in my pocket. I pulled it out and saw I had received an e-mail. I opened the message, and saw that it was from a girl who found my profile on the website.

The e-mail said that my profile intrigued her, and she wanted to get to know me. I was not having any fun at the bar, so I went home and fired up my computer. I quickly booted up my e-mail and sent a quick reply to the girl. The girl, who called herself Ally-cat, was obviously still online, because she replied to my e-mail quickly. Over the next couple hours, Ally-cat and I traded e-mails. We seemed to really hit it off and had a good connection.

I had made sure to not post my picture on the site, for fear that one of Natalie's friends would find it and the situation would be too awkward to explain. Ally-cat had likewise not posted any photos of herself. When I finally felt comfortable enough to trade pictures with her, I asked Ally-cat if I could see what she looked like. Her response surprised me. It was the longest I had waited before receiving a response from her, about 45 minutes. I thought I had scared her off, but when I finally got a response Ally-cat told me I could see what she looked like when I met her in the hotel bar across town the following night.

I was initially surprised. I knew she and I had seemed to hit it off and had a good connection, but I did not expect her to purpose a meeting so quickly, if at all. But the website we met on was designed to find people to hook up with, and I guess that's really what she wanted. The more I thought about it though, the more excited I became. It was just drinks right? Or was it? I decided to accept and see what might happen.

I went to the agreed upon hotel early the day of the meeting. I had told Natalie I had to go overnight for work and would be home the next day, and got a room at the hotel. I was not sure if I would be sleeping there alone or not, but decided it would be a good idea to have just in case things heated up.

I was supposed to meet Ally-cat in the bar at 9:00. I purchased a single red rose earlier and left it with the bar tender with the instructions to give it to a girl when she came in asking for me. I had explained this to Ally-cat when I accepted her invitation earlier. I sat in a booth toward the back of the bar with a good view of not only the bar, but the front door as well.

Time went by and several girls walked through the door and went toward the bar. A few of them I thought were very attractive, and found myself hoping the bar tender would hand them my rose, but he never did. 9:00 came and went, and still no one was given my rose.

It was about 9:15, and I was just beginning to think Ally-cat would not show when I saw a girl walk into the bar. My heart suddenly began pounding in my chest. I was sure she could probably hear it across the busy bar. It was one of Natalie's good friends, Allison.

"Oh my god" I said to myself. "She can't see me here talking to another girl." I began thinking of a way to sneak out of the bar without her seeing me. Allison looked around the bar for a moment, and then she walked toward the bar. I thought that while she ordered a drink would be my opportunity to sneak out, so I watched her as she went to the bar tender and began talking to him. Suddenly it felt as if my heart exploded.

The bartender handed Allison my flower! I had not put it together till that moment, but obviously Ally-cat was short for Allison. After handing Allison the rose I had left for her, the bartender pointed directly to where I sat. Allison turned and saw me. I was stuck. There was no sneaking out now. Allison froze in place. She had a shocked look upon her face, one that probably matched my own.

I did not know what to do. I did not know what Allison would do. Would we just stare at each other all night? Allison made the choice first though. She began walking toward my table.

As Allison crossed to bar toward me, I allowed my mind to wonder. I had always found Allison attractive. When I first began talking with Natalie again, and we discussed starting a relationship, she told me I would need to meet, and get the approval of, her friends. In a joke among them and me, I was told to "beware the little one". The "little one" referred to Allison and her height of only about 4'7" tall. Allison was a slightly plump girl with gentle curves that I found not unattractive looking. She had straight blonde hair that came to just below her shoulders, and light blue eyes. She had a cute round face with a slightly upturned nose. She was not what most people would call drop dead gorgeous, and not the most attractive of Natalie's circle of friends, but she was good looking and I do recall myself checking her out on more than one occasion. Tonight Allison wore a little black dress that came down to just above her knee and showed off her curves very nicely. The dress was held up by two thin straps on each of her shoulders. She was wearing black stockings and high heeled black shoes. Although my heart was pounding intensely and I was scared about what would happen next, I could not help but think how good Allison looked that night.

She weaved her way through the people in the busy bar and came up to where I sat. She sat in the booth across from me. Neither of us knew what to say.

"Umm... hey" I finally said

"Hi" Allison replied, obviously as nervous as I was.

Allison, from what I knew, was in a long term relationship with a guy named Ben. Ben had actually been one of the nicest of the group toward me when I first moved to town; always talking to me and making me feel welcome. But things were not always great between him and Allison. Allison lived with Ben when I first moved, but recently she had decided to move out. She moved back in with her parents, but was still with Ben and stayed with him on the weekends. At least that is what I thought the situation was. Obviously Allison was looking for more than Ben gave her, and that brought her to my table in the hotel bar.

"I guess this was for me?" Allison added, indicating the single rose she held.

"Yeah it is," I said. "I sure did not expect you to be the one who got it though."

After seeing someone else join me, a waitress came over to our table. We ordered a couple of drinks. "We're going to need them," I thought.

Neither of us still knew just what to say, but I realized we had to talk about this situation. We both knew why we were here, so I decided to not beat around the bush.

"So things aren't going good with you and Ben?" I asked.

"I don't know..." Allison answered. "I do think I love him, you know, it's just he never seems to want to have sex with me, and when we do its way too short and not very good."

"So you're cheating on him?" I asked.

At first Allison was taken aback by my accusation. "Well this would have been my first time," she said, looking down at her drink instead of at me. Then she suddenly looked up at me and added "What about you?! You're cheating on my friend!"

"Calm down," I said. "Natalie cheated on me first. This is our way of keeping things fair I guess. I know it sounds crazy, but she is fully aware of this and is ok with it."

"Oh," Allison responded. "Doubt she would be ok with it being me though."

"Well, probably not," I answered. "But that's why I tried to find someone I didn't know online." Then I added, "What about you? Why would you want to do it with a stranger?"

"I don't really know," Allison replied. "I guess I'd rather it be with someone I knew, but I didn't know how else to go about finding someone to have an affair with" she said mater-of-factly

We both laughed. I could tell we were both very nervous and did not know what to do next.

"What about you?" she asked. "Why would you rather be with a stranger?"

I said, "To be honest I wouldn't, but I don't know many people up here yet. I would rather it be with someone I knew actually. Someone I had always thought was very attractive." I looked Allison up and down.

I could not believe what I had just said. Maybe it was the alcohol, maybe it was that I had intended to have sex that night, or maybe it was that deep down I had always had some feelings for Allison. Allison looked back at her drink and noticeably blushed. I knew that I was playing with fire and needed to get out of there before I did or said something that would burn me.

"Well look," I said "I know this isn't what either of us wanted or expected. I guess we just go our separate ways and forget this ever happened." I started to get up from the table. I reached into my pocket to pull out money to pay for our drinks and happened to pull the pair of hotel door keys out as well.

Again I do not know what I was thinking, but what I said and did next I think took both of us by surprise. I laid one of the keys down on the table and slid it toward Allison.

"I'll be up there alone all night," I said. "If you want to join me, you're more than welcome"

Allison looked at me, shocked. She picked the key up and studied it like it was a rare relic.

"Room 217," I said, than turned and walked away without another word.

.

I rode the elevator up to the second floor and walked to my room. I used my one remaining door key to gain access to the room and closed the door behind me. I stood there for several moments with my back against the door, more than once hitting my head backward against the hard wood of the door.

What the hell was I thinking? Any chance I had of Allison not telling Natalie about this encounter surely flew out the window the moment I invited her to my hotel room.

"Unless she actually came up here," I said aloud, knowing there was no one there to hear me. The idea that she might actually come up to the room to be with me was such an exciting one that I immediately moved away from the door, imagining I might be preventing her from opening it.

Not surprisingly, though, the door did not open. I sat on the bed and turned the television on. I flipped through the channels randomly, paying more attention to the un-opening door than the t.v. screen. After what felt like hours, but was really only about 45 minutes I decided she was not coming. I knew it was a hopeless dream anyway.

"She did look very good in the little black dress," I thought to myself, but I knew it was foolish. I got up and went to the bathroom to take a cold shower. I turned the television set off as I walked by.

I let the cool water wash over my heated body. It felt good. I was racking my mind trying to think of ways to tell Natalie about me inviting one of her best friends to my hotel room. I had a license to cheat, sure, but with a friend? I knew that was another thing entirely.

Finally I realized I had spent enough time trying to wash my troubles away and turned the shower off. I stepped out of the shower and grabbed a towel from the rack above the toilet. I began to dry my hair, listening to the movie playing on the television in the next room.

It was not until I heard the channel change that I realized I had turned the set off before going for my shower.

"Great," I thought "on top of everything, my room is haunted." I wrapped the towel around my naked waist and opened the bathroom door. I walked into the hotel room and was shocked by what I saw.

Allison was sitting on the bed. She looked at me as I entered the room. Seeing my lack of attire, Allison looked me up and down, taking in the sight.

"I didn't think you were coming," I said as I began walking toward the bed.

"Well," she responded "I wasn't going to, but the more I thought about it I realized you were right. I would rather do this with someone I knew."

"Oh, is that so?" I asked.

"Yeah," Allison answered "someone I know won't hurt me or anything. And someone I know can give me what I need."

I was not sure what she meant by that last comment. "And I can give you what you need?" I asked.

"Well, Natalie did tell me about your um... gifts" Allison said.

I was a little shocked that Natalie had been spreading the word about my size. But girls will talk I suppose. I said to Allison "Oh she did, did she? Well how do you know she was telling the truth?" At this point I was standing next to the bed. Allison turned so she was sitting on the edge of the bed directly in front of me.

"Let's find out" She said. Allison reached up and undid the towel from around my waist and let it fall to the floor.

As I stood nude in front of Allison, she ran her hands up my legs. Her hands began to near my crotch. I was surprised we had reached this moment. This evening had been a roller coaster of emotions, and deep down I still felt a sense of trepidation about committing the act with someone so close to my girlfriend. Allison's hands reached my penis, though, and I pushed all the fears I might have had from my mind and enjoyed the moment and the sensations I was receiving.

The fingers on Allison's right hand began to encircle my shaft while her left hand cupped my balls and began to gently roll them. Allison did not take her eyes from my crotch as she began pumping on my shaft with her hand. I grew hard in her hand, the feeling of her hands on my privates very intense. Slowly Allison raised her gaze to me, and our eyes met. She had a look of fiery passion in her eyes.

Allison's eyes fell back to my now hard penis as she continued to jack it off. Then she leaned forward and her pumping motion slowed. Allison held my shaft upward and leaned in to lick the underside of my penis from the base just above my balls all the way to the tip. Her tongue swirled around the head, before going back down the side to the base again. Allison's licking felt wonderful on my hot shaft. After a couple more trips up and down my shaft, Allison continued her pumping of my penis, aided now by her saliva which coated my shaft.

Then, to add to the pleasure Allison was giving me, she leaned forward once again, and this time took the head of my penis into her mouth. She began to suck on the tip of my penis while her hand continued to jack me off. I moved my hand to the back of her head and applied a small amount of pressure. I started to moan loudly. Allison could not take a large amount of my thick penis into her mouth, so I let her suck on the head as her hand began to twist around my shaft as she pumped. I was amazed that, although she could not take very much into her mouth, she made up for it with her hands, and it felt incredible.

Although I was enjoying this very much, there were other things I wanted to with Allison before the night was through, and time was already not on our sides. I took my hand off the back of Allison's head, and took her hands. I pulled her to her feet and kissed her mouth. Our tongues met and danced around one another, moving back and forth from her mouth to mine. My hands began to explore her body, starting first at her soft backside. I squeezed her amble butt cheeks with both of my hands as we kissed. Then I moved my hands up her body. I lightly grazed over her breasts, at which point she let out a light moan, but they were not my target, not yet. My hands continued higher till I reached her shoulders. My fingers wrapped around the straps of her dress and lightly fell to the sides, pulling the thin straps away with them. I released my hold on the straps and pulled back from her, allowing Allison's dress to fall to the floor around her feet.