One day while sitting at my desk, my boss comes to me to ask me to make a trip to Chicago. We have a customer there that is having some problems, and he wants to smooth things out. I am a technical person, and not the one in charge of this site, and he confirms that someone will be going with me. Now, there are only a couple of people from my office that I would not mind taking a trip with. Luck was with me, as I get paired up with one of them. Her name is Amber.

Others might disagree with me, but I think she is one of the most attractive women in the world. Not saying that she is the most beautiful, though beautiful she is. She has long, blond hair which is always wavy. She loves to pull it over one shoulder, and that gives her a very exotic look, especially when she has a tan. She has tiny butt with a nice curve to it, and her breasts are bountiful. She has a habit of being away from her desk when expecting a phone call, and I will be blessed with the sight of her running past me to answer it.

I go to her desk, and discuss the plan for going to Chicago. Our office is only a few hours from there, so the plan is to drive. I told her I would be willing to take my car, and she agrees. The morning of our departure, I meet her at the office before sunrise. I help her load her suitcase into the trunk, and we hop in, and take off. We begin the trip by discussing what we expect to come up against first with this customer, and we move along with a plan to address about everything we expect the customer to throw at us.

We expected this to take the majority of the time driving, but took about an hour. I grin and say that if anything, we are good. She chuckles at my attempt to humor her, and we grow quiet while the radio plays. After a short while, we begin discussing the local weather, and I listed to a little of her gossip from the office. From there, we start talking about the colleges we went to. We shared some stories about parties, classes, and general college life. She is not a shy person by any stretch, and it seems that she was the social butterfly back in college as well.

As it appeared that our college discussion was winding down, she asked me what the craziest thing I had ever done was. Not being one that sees a hint, and not wanting to upset her from the onset of this trip, I decide to tell her about this truck I had, and running Chinese fire drills. I knew it was lame, and her patronizing chuckle told me so. I asked her the same question. She mocked me by retelling my story. That made me a little angry, so I told her that I did not want to offend her. If she wanted to be the first to open up to that question, I would do the same.

With a grin, she told me that the summer after graduating high school she had been gang banged. I looked at her with obvious shock. She told me not to judge her, as she was wanted to do it. I told her I was not judging her, but I had not expected that. I probed a little, asking if it was one at a time, or multiple. Without batting an eye, and with absolutely no humility, she told me it started out with multiple guys. At one point, she said she had one in her pussy, one in her ass, and was jerking off two others. By the end of the night, she said she had sex with eight guys, but as outstanding as it was, she doubted she would ever do it again.

Now she wanted to know about my craziest thing. I told her about a time I took a week from work severally years before I started working here, and I started driving. I did not know where I was going, but I was just going somewhere. She got an incredulous look, but I told her to bear with me. I had found a small town that was having a wine festival, so I decided to stop in. The town felt like something from another time, except for the cars. Old buildings, the town set against the hills and a river. The people there were nice.

While wondering around, I happened to be approached by a couple of girls that were wearing college sweatshirts. We chatted, and I had taken a liking to one in particular. They told me that they were from a university about 45 minutes away, and they were just starting their senior year. At least they were not planning to use me to get them alcohol. I spent the day with them, having a great time. When night fell, I had had too much to drink, but was not falling over. The one I had an interest in asked me right out in front of her friend if I wanted to go back to her dorm with her. I said sure, but I could not drive. Her friend took my car, and followed us back to the dorms. While driving, I started getting frisky with her, rubbing my hand up her thigh, and under her shirt. She moaned and sighed. We got to the parking lot, and her friend have me my keys, and while heading for the door, looked back and told us to keep it down since she had to be up early for work.

I looked at the one I was with; her name was Amy, by the way. I asked her if they were roommates, and she told me no, but they shared a wall, and bathroom. In fact, she did not have a roommate this year. We stumbled into her room, and she pushed me onto her bed. Before anything else, she started stripping me down, and crawled between my legs, and started sucking on my cock. The surprise here came when she snaked a finger inside of my ass. This had never been done to me before. I groaned as she massaged my prostate, and licked the head of my cock. She took her mouth from me, and asked if I was enjoying it. I told her that I was, and she went back to work. Before I had a chance to cum, she stood up, and slowly stripped out of her clothes. She crawled back into bed, but we were not in the 69 position. Something else I had never done. I began licking her pussy. She was very wet, and her musky smell was driving me insane. She again worked a finger inside of my ass while she sucked on me. I reciprocated, and put a finger inside of her asshole while I ran my tongue over her clit. She had a quick orgasm, and slid down, spun around, and started to rub her wet pussy over my hard cock.

It was torture, and I asked her to put it in. She told me not yet, and lay beside me. She said she wanted more of my tongue inside of her. I knelt between her legs, and went back to work. After a few minutes, she asked me if I would be willing to try something before I fucked her. I said perhaps. She said that her friend's boyfriend was bi, and she wanted to watch him fuck me. This was a shocking turn. I was so horny now, I was not thinking clearly, and definitely not with the correct brain. I could not believe that I replied by asking what all she was talking about. She pulled my face back to her pussy, and said she just wanted to watch his fuck my ass. From between her thighs, I asked if I could keep doing what I was doing while it happened. She said she could not watch, but maybe I could with her friend. I said I would do it, but under those conditions, and that I got to fuck her ass as well. She squealed with delight, and jumped out of bed. Without covering herself, she went into the bathroom, and into her friend's room. After a few minutes, her friend, and a guy walk into the room completely naked.

I say that I want her to lay down, so I can get comfortable with her. She did, and I crawled between her legs, and started at her breasts. They were magnificent. Even better than the one who set this all up. I suckled her nipples for a few minutes, and kissed my way down her belly. I went right past her pussy, and began kissing her thighs. I looked up at her, and I asked her if she enjoyed her boyfriend being with other men. She nodded her head, and I began attacking her pussy. She was extraordinarily wet. She began moaning loudly at my attention. At this time, I felt something wet around my ass. A quick look back and I saw that the guy had his face there, and was licking me. I started to question the sanity of my decision, but a look to Amy, who was rubbing herself made me think of other firsts to come.

Soon, the guy moved away, and I felt a finger pressing into my ass. It was lubed up, and he was working it all over. I heard Amy say that I had never done this before, so to be gentle. Her friend pulled my face up, and asked if that was true. I said it was, but to have a chance to taste her, and have Amy's ass, it was worth it. I took that moment to slide a finger in her ass, then another. She ground herself against my face. It was then that I felt the guy, whose name I did not know, crawl onto the bed, and he put a hand on my hip. Then I felt him place the head of his cock against me asshole, and start to push. It did not take much, but I felt it pop inside, and there was a stinging pain. I tried to focus on the pussy in front of me to take my mind from the pain. After a moment, he started moving in and out. The stinging was still there, but the moving did not make it worse.

Soon, he was working his way deeper, and I felt pressure on my prostate. This caused me to groan, which was followed by Amy's friend groaning, and soaking my face with her cum. She crawled from under me, and stood next to Amy to watch me get my ass taken. With a groan from behind me, I felt the rest of his cock get slowly forced inside of me. The pain was gone now, and he was able to move freely. Once in, he started diligently fucking me. When the head of his cock would rub over my prostate, I felt like I would explode. I could not believe that I was actually enjoying this. Soon, he was moving faster, and pulling out as far as he could, only to push back in all the way. Amy's friend reached under me, and grabbed my cock, and started gently squeezing it. As soon as I felt the guy start thrusting erratically, she started stroking me. With several grunts, I started cumming, and I guess that he was not far behind.

I did not move for a few minutes, not until he pulled out from me, and I heard the door close. Amy nudged me over, and took my cock in her mouth, and cleaned me up. She said that that was the hottest thing she had seen, and thanked me for doing it. She had me hard again, and lowered her pussy down onto me, and started riding me. She was very wet. She kept asking me how I felt, and how it felt when it was happening. I told her that it had been exciting. She started telling me about how it looked to her. I could still feel him inside of me, and soon, I was cumming inside of Amy. She settled down on top of me, and asked me if I still had enough left to finish our deal. My cock started to grow at that. I had never fucked a girl's ass before. I never thought I would have had mine fucked before that, or ever for that matter.

She started rubbing herself on me, and I become fully erect. She took some lube and handed it to me, and got on all fours. I told her I wanted to watch her do it. She grinned, and put some on her fingers, and started to run around her asshole. I watched as she slipped a finger inside her ass, and pumped it in and out while moaning. Moving behind her, I asked her if I should go slow or fast. She said slowly, as she has only done it once before. Kinda like me I said. She giggled at that.

I pressed against her ass, and after a couple of attempts, the head was inside. With her head lying on her pillow, her eyes went wide. She let out a curse, and then begged for more. I did to her like was done to me; I slowly forced the entire length of my cock into her ass. I pressed into her, and just held it there. I could not believe how tight it was. There was constant pressure on all parts. After holding there, she breathlessly asked me to pull out almost all the way. When I did, she pushed a small vibrator inside of her pussy, and turned it on. When I pushed back in, it was even tighter, and I could feel the muted vibrations. I held myself there again, and she demanded that I start fucking her. I pulled out, and told her I needed more lube. After adding some to my cock, I push back in, and began fucking her ass in earnest. She was squealing like crazy. I glanced over to the door, and saw Amy's friend in the room again. This time, she was fucking herself with a vibrator with one leg on a chair. I had a nice view of it going in and out of her. I looked back to Amy, eyes still wide open, mouth gaping. I told her that I bet she liked having her ass fucked more than she liked watching some virgin guy getting fucked for the first time. That did it, she squeezed her eyes tight, and her jaw clenched.

I felt her ass clamp down on me, and I told her that she was going to cause me to cum in her ass. Her body was twitching, and she was making all sorts of noise. I felt something behind me, and as soon as Amy's friend pushed her vibrator up my ass, I started cumming. My hips thrust involuntarily, and I pressed deeper into Amy's ass. After some more twitching for us both, her friend removed the vibrator from me, and I stood on wobbly legs. Amy stood as well, and I pulled her back to me, kissed her neck. My hands reached around, and I fondled her nipples. Her friend came to us. She put one hand to my ass, and one to Amy's pussy, and kissed us both, telling us how hot that was. She thanked me for being a good sport, and then went back to her room. Amy and I tore the covers off of her bed, and fell asleep. I left the next morning, and never saw them again.

While telling this story, I noticed my passenger has become a little fidgety. I looked at her, and she was flushed. I said that there was my story; I let a guy fuck my ass so I could get it on with a couple of beautiful women. I was willing to take anal sex in order to give anal sex. I kept making statements like that, and she finally said that I had to stop. She was breathing hard, and her skin was nearly pink.

We get to Chicago, and do our work and head to the hotel to get checked in. As usual for these trips, we are on different floors. Too bad, I am thinking. It would have been a great time for adjoining rooms. I get a call from her in my room asking where we should have dinner, and go over what we accomplished that day, and plan for tomorrow. There is a diner not too far, so we decide to walk down there and eat. Nothing is said sexually, it is all business. We are walking back to the hotel, and she notices a strip club. I noticed it as well, but was not going to say anything. She says, let's go in. I just stop, and look at her. She gives me the look that I saw in the car after my truck story. I say OK, and she leads me inside.

Once inside she is commenting on all of the women and their assets. After awhile, she confides that she would love to take one back to her room and try lesbian sex, but doubts any would be interested. After some more dancers come and go, one comes over and starts chatting us up. She and my coworker are whispering to each other and giggling. Finally the stripper tells her to give me a blow job, right there. I give them a shocked look. She dancer says that I am obviously up for it, and looks to my crotch. I am rather swollen in that area.

Amber is getting giddy, and giggling every time the stripper tells her to just get down and give me a blow job. I finally can't stand it anymore. I tell my coworker to sit on the stage. She gives me a look, asking what I am doing, but does it anyhow. I grab her legs and lift them, causing her to roll backwards on the stage. I lift her skirt up as high as I can and grab her panties and start pulling them off. Again she asks me what I am doing. I say, since you cannot make up your mind about giving me head, I am going to give you head. I then tear her panties off and go down on her. She was not wet to start with, but soon, she was rather humid down there. I was getting off on her musky scent and she is going crazy. We are also starting to get a crowd around us.

I pull her up and tell her we better get out of there, right away. We leave and once outside the door, she pushes me against the wall of a building and kisses me. We then walk arm in arm back to the hotel. She starts to giggle, and tells me that she left her panties back in the strip club. I reach behind her, and quickly lift her skirt up, showing anyone behind us her bare ass. She squeals and slaps my arm away. I tell her point blank that I want her.

We get back to the hotel and go up to my room. I can tell she is getting nervous, so I pick her up and sit her on the desk and resume licking her pussy. She is very wet now. I lick her to an orgasm, and then help her up. I turn her around, and have her lean over the desk a little. Pulling up her skirt, I start to put my cock in her ass, but it is tight. I run into the bathroom and get some lotion, expecting her to either be ready to leave or in some other position, but she is still there, bent over the desk, ass in the air. I lube up my cock and start to slide it in again. I get inside and start slowing moving in and out of her ass. The feeling is outrageous. I am really getting into this. After a few more minutes, I blow a load in her ass. When I pull out, she turns around and starts kissing me. I suggest that we stop and take a bath together, to which she readily agrees.

In the tub we caress each other, playing with each other. I can see she still has a hungry look so we get out of the tub. Without drying off we proceed to the bed. I try to get her to lie down, but she is resisting me. I finally push her roughly onto the bed. She crawls back a little ways and spreads her legs for me. As I start to move towards her, she begins fingering herself. I stop and watch for a moment while she rubs her clit and then puts a couple fingers inside. God, I want to fuck her again. I crawl between her legs and remove her had. I pretend like I am bringing it to my mouth, but then instead move it towards hers. She seductively licks her fingers.

I line my cock up at her pussy and lunge inside of her. We then proceed to fuck our brains out. No feelings involved, just me sticking my cock in her pussy. She is grunting beneath me, and I can feel her pussy getting wetter. After a time, I get on my knees and put her legs over my shoulder and start ramming her as fast as I can. She is nearly screaming at this point. I can feel her juices coating my balls. I am trying my best to make her cum before me, but I am losing control. I finally start shooting my load inside of her, and she lets out this guttural moan and starts shaking. I can feel the inside of her pussy convulsing around me.

That was absolutely the greatest orgasm of my life. She finally pushes me away, and I lay down on my back. She curls up with her head on my chest, and we lay there cuddling until we fall asleep. I wake up a little later and hear her lightly snoring. I start teasing her nipple. She starts to wake up and I roll her over, and we start at it again. This time it is closer to making love than fucking.

We have passionate sex for about 30 minutes. Strangely enough, when she climaxes, she starts squealing and screaming this time. After she finishes orgasming, she rolls me onto my back and proceeds to give me a very nice blow job. It did not take much longer before I was cumming in her mouth.