Better Days for Michelle

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1-1: INTRODUCTION

This story takes place in 1998, back when the internet was in its infancy and the world seemed like a far more innocent place.

In college I was a business major and a psychology minor. During one of our psych classes we reviewed a detailed study on how men and women were different. One way is that women tend to be sexually content with one partner, as long as that partner satisfies her needs. But a man's biological tendency is to desire multiple partners, even the men who ultimately remain faithful to their spouses.

Of course, my female friends in the class took this as evidence that "men were assholes" but I looked at differently; how can men be blamed for wanting multiple partners if that's simply the way nature wired them?

My name is Michelle and I've had it good my entire life. My parents had enough money to send me to a prestigious college, and I had the smarts and work ethic to make the most of it. I'm also lucky enough to have always been considered attractive, and with a nice figure. I'm five foot six, and about 125 pounds, with blonde hair and curvy, size 36-C breasts. Unfortunately I was a bit clumsy from a sexual perspective. I was very picky about men, and by the time I'd graduated college I'd slept with a grand total of two guys. Neither of them were exactly spectacular in the bedroom, and I saw sex as something a woman just had to go along with to maintain a relationship.

1-2: MEETING TRENT AND JOHN

After graduation I got a job and I moved into a townhouse with two female roommates and started my new life in a strange new place, a small city in Massachusetts that was about an hour from my home town.

One night I went to a bar with some of my new friends from work, and met a guy named Trent. He innocuously started up a conversation with me and I thought he was cute, both in looks and demeanor. As my friends and I left he asked for my phone number, and I figured "why not"? After a few phone calls we went on our first date. He was good looking and nice enough of a guy, but he didn't really press my buttons. Still, having a guy take you out to dinner and a movie or whatever was better than staying at home every Saturday night. We dated for over three months before I finally slept with him. Just like Bachelors #1 and #2 before him, it was nothing special.

For the men reading this, I've already let you in on one awful secret- there are occasions when we go out with you only because you're better than nothing. Another awful secret is that sometimes we develop crushes on your friends.

This specific crush started when Trent and I went on a double date with his friend John and his girlfriend Kathy. Nicknamed "Johnny Mac", he was really good looking with a handsome, tanned face and a great physique- but more than that I found him to be incredibly charismatic. He worked in sales for a software designer and was doing quite well, as evidenced by the expensive sports car he drove.

Trent, John, and I were all college educated and in our mid-twenties, which made Kathy stand out in the wrong way. She was only nineteen years old, but John had somehow secured her another person's ID that said she was over twenty-one. The man could get things done, another turn on. I just didn't think she was that pretty. She was cute enough, but she was short and while she was thin, her breasts were rather small. I could not imagine what he saw in her. She didn't strike me as someone that was particularly smart, either.

After dinner and drinks we went to a comedy club and then said our goodbyes. John gave me a hug and said that "it was nice to finally meet me," and when he did the breath practically left my body. As I walked with Trent toward his car, I discreetly turned around and took one last look at John... just in time to see him turning his head toward me. We made eye contact and he shot me a confident smile that made me shiver. When Trent and I went back to his place I made love to him as passionately as I ever did with a man in my life. Trent naively wondered what had gotten into me as I actually got on top of him and rode myself to an orgasm just before Trent came inside me. Afterward, Trent and his limp dick were asleep within ten minutes. It was frustrating; for the first time in my life all I wanted to do was fuck, and I was stuck inside the apartment of my sleeping boyfriend.

Two weeks later we went out on another double date with John and Kathy. The sparks between John and I were obviously flying. I could tell Kathy noticed, but Trent just didn't and for whatever reason I couldn't help but be resentful of him over it. This wasn't like me, but I couldn't get John off of my mind. Not only did he have a girlfriend, but he was one of my boyfriend's best friends. It would be wrong to do so, but it was all I could do to refrain from calling him and asking if he wanted to get together, discreetly. Trent asked if I wanted to go out with John and Kathy again, and I said yes despite knowing that any encounter with John could lead me further down that road of temptation.

1-3: THE NEW KATHY

When we finally got to the restaurant, I saw that Kathy's appearance had radically changed. Instead of her shoulder-length brown hair she now sported a shorter, spiked look with one long lock remaining that was dyed bright pink. She now had four hoops in one of her ears, a shiny stud in one of her nostrils and was wearing a lot of mascara and lipstick. She looked really slutty, and that's without taking into account that she was also wearing an incredibly tight, short black dress that actually looked uncomfortable, especially since she was constantly fidgeting with the hem of it, making sure that it didn't come up high enough to show her ass cheeks. At one point John put his arm around her and the skirt came up enough to not only display the bottom of her cheeks, but to show she wasn't wearing any underwear! Kathy's face was pink with embarrassment, but John seemed to be enjoying himself.

John invited Trent and I to his place for a few drinks after dinner. While I accepted, something seemed to be off and I actually felt kind of nervous. I'd never been to John's apartment before and I shouldn't have been surprised that it was immaculate. He'd hired an interior decorator and the place looked fantastic. Of course he had a huge TV, a high-end music system, a magnificent salt water aquarium, the works. John also had a wet bar and he made everyone some tasty but strong drinks. John, Trent, and I were talking and laughing for about an hour. I was definitely feeling a buzz, I think we all were. I noticed that Kathy had remained relatively quiet and seemed focused on drinking as much as she could. Trent tried to break the ice by complimenting her on her new hairstyle and then he asked her why she decided to get all of the new piercings. What were there, five new ones since the last time we'd seen her?

That's when John cut in, smiling and saying those weren't the only piercings she got. I wondered what he was talking about when he asked Kathy to stand up, and as she did the look on her face was unmistakably nervous.

"Michelle, would it be OK if Kathy showed you guys her breasts for a minute?" John asked.

As the words came out of John's mouth I tried not to gasp. I felt like I had no reason to object so I just meekly said, "Um...sure."

Kathy looked panicked as John stood behind her and unzipped her dress, and then slowly lowered the straps down to her waist. She wasn't wearing a bra and her small 34-B breasts had large pink nipples that pointed out like pencil erasers.

The electricity in the room was palpable as John stood behind Kathy, massaging her breasts. She was till terribly nervous but you could tell that John's manipulations were getting her hot. I have to admit, the entire scene was turning me on a bit as well.

Trent chimed in that it looked like Kathy had wound up getting seven piercings (look everyone, Trent knows what five plus two equals)! John kind of laughed and said, "No, actually...ten."

And with that John lowered Kathy's dress to the floor. The first thing I was taken aback by was that she had no hair on her vagina. While I tried not to stare but I couldn't help but noticed that there were two circular piercings on the outside of it on the right. John pulled her to one side so that she stepped out of her dress. Kathy was now completely naked except for her high heeled shoes. John instructed her to sit on the coffee table in front of us and she complied. As she sat facing Trent and I, John pulled her legs back and then spread them wide open into a pose that could accurately be described as obscene. A trip to the OB-GYN wasn't this revealing!

John mentioned that last weekend he had Kathy get a total of ten piercings, and the final one was on her clit. I looked and saw the small stud that Kathy had inside her. I also noticed that the entire room smelled of sex- Kathy was totally getting into John showing her off in such a manner. I glanced over at Trent, who couldn't take his eyes off Kathy's shaved and pierced pussy. I looked down at his crotch, and he was as hard as a rock.

Then I glanced at John's crotch. I could tell by the outline of his pants that he wasn't completely erect, but that he was packing something big there. I looked up at his face and he threw me that sly, confident smile. He'd caught me looking, and I could tell he knew that I liked what I saw.

I looked back down to Kathy, who was breathing hard. I was then completely startled by the next words I heard from John's mouth: "Do you guys want to swap?"

My head was absolutely spinning. Part of me was insulted by such a proposition; what was I, some kind of a slut that would just jump into bed with John while my boyfriend screwed some pierced-up little whore? Another thought quickly crossed my mind. I WANTED to be with John. This way I could have him without going behind my boyfriend's back, and without having one of Trent's best friends betray him. It would all be out in the open. Then I remembered how men are psychologically structured- of course Trent would want to do it.

There was no way I was going to take responsibility, so I looked over and told Trent "It's up to you." Trent asked if I was sure I was OK with it, and I tried to be flippant. "Why not?" I said with a smile, "Go show her the time of her life".

1-4: A FIRST TIME FOR EVERYTHING

Trent seemed pleased with that answer and I then felt someone else's hand on my own as John took me by my hand and pulled me toward him. I stood up, looked right into his dark brown eyes and involuntarily licked my lips. This was the moment I'd been waiting for, the one that I was afraid would never happen.

After what seemed like an eternal wait, John pulled me closer and started kissing me. I kissed him back for all I was worth. As our tongues probed around in each other's mouths I felt him grab my ass and direct our crotches together. He was so big and so hard! I was really getting into him and grabbed his ass as we started to dry hump. I could barely contain myself as I started whimpering and groaning in lust. I had never, ever grabbed a man's cock through his pants before, but there's a first time for everything and I started groping John's cock. I couldn't wait to get him out of his clothes.

We both looked over at Trent and Kathy, who had barely moved since this all started. Kathy was still lying on her back on the coffee table, but Trent was now eating her pussy. John whispered in my ear that it was time for us to go into the bedroom. As we headed toward that door John gently instructed Trent to use a condom.

What happened from there is kind of a blur. Part of me wishes there was more foreplay and anticipation before we had gotten out of our clothes, but they were almost immediately flying around the room. I didn't even bother asking John to turn the light off, which was generally a requirement with me. Before I knew it we were both naked with John on top of me, taking plenty of time to kiss and lick my neck, my breasts, and my stomach, all while occasionally taking the opportunity for a long, passionate kiss. It was already the best sex I'd ever had, and it hadn't even started.

John then started kissing and licking my legs and thighs, getting closer and closer to my pussy. He took forever doing it and I began to get a bit frustrated. I realized that he was expertly teasing me, getting me hotter by the moment. Every other guy that ate me out just dived in, but John made me desperate for it. As I lay back anxiously awaiting, I wondered if this was the first time John had used his savvy to make me want him.

Before long he had his tongue darting in and out of my wetness. God, he was so much better than anyone else I'd been with, changing rhythms and speeds and occasionally sucking on me. Before he was done I'd achieved four long, loud orgasms that I was certain Trent and Kathy could hear in the other room. John eventually pulled me up for a kiss. Usually I didn't enjoy a guy's tongue going straight from my vagina to my mouth and would sometimes object, but in this case I didn't care. In fact I enjoyed tasting my own juices in John's mouth.

I reached down and grabbed his dick. It was so big and so hard, about eight inches with a head that truly stood out. I always liked the idea of sucking cock better than the actual act itself. When I was alone I would sometimes fellate a banana or a popsicle while fantasizing that I was sucking off some sort of a dream guy. This time, the reality was far better than any fantasy. I put as much of John's cock into my mouth as I could while using my right hand to masturbate the bottom half of his penis. My grunting noises filled the room as I sucked off his delicious manhood.

That went on for about five minutes before John rolled around and placed himself on top of me. Even though I used birth control, I had always insisted that all of my lovers wear condoms but not this time. If John wanted to go bareback, that's exactly what we were going to do. As I felt him begin to enter me I cried out, and meekly said that I was afraid I was "too small down there" for him to get himself in. He confidently told me not to worry, that he knew just how to do it. He wasn't just being cocky, as his words were reassuring.

Suffice to say that by the time we were done, I was screaming uncontrollably and enjoyed several more orgasms. John's cock found places inside me that had never been explored before. The guy just knew how to fuck; he would speed up, slow down, change his rhythm, and would sometimes stop entirely, leaving me desperate for more.

There was a clock radio in the bedroom, so I knew it wasn't my imagination telling me that we'd been at it for over 20 minutes before he finally shot his load inside of me. It was an incredible feeling I'd never had before, having a man fill my pussy up with his hot cum. By the time he finished I was in another world.

1-5: "IS HE REALLY GOING OUT WITH HER"?

After we finished, John held me while I cooled down. We began kissing again. It was just awesome, like something from out of a dream. As I lay in his arms I finally just had to ask, "Please don't take this the wrong way, but why are you going out with Kathy?"

John just kind of laughed and he relayed the story. Kathy used to work part time in the mail room where he was employed. She had a big crush on him, and long story short they would up having what he thought would end up as a one night stand. A few days later she called him saying that she so desperately wanted a relationship with him that she was willing to do literally anything he said with no questions asked. John said this started off well but as time went on Kathy was drifting further away from her 'anything he said with no questions asked' pledge so last week he took her to a place in New Hampshire that did all of those crazy piercings, as a way to remind her who the boss was. He then took her to a stylist with a picture of some punk rock chick and had her replicate that look. Having her show the piercings off to Trent and I, among other things, was yet another way of reminding her who was in charge, testing her limits. He'd already had her fuck a couple of his other friends so letting Trent have sex with her wasn't an issue.

At this point I reached for my underwear and John asked me what I was doing. He followed that up with "I'm not done with you" and I melted- there was more to come! But I really needed to pee, and felt weird parading around naked. John told me not to worry about it. Trent had already seen me in the nude, and it didn't matter if Kathy did.

1-6: YOU GOT A SPRINT, I'M GETTING A MARATHON

Regardless, it still felt weird emerging from John's bedroom wearing nothing but my birthday suit. As I quickly passed Trent and Kathy I noticed that they were watching TV while sitting on opposite ends of the couch. Trent was already dressed and Kathy was wearing an over-sized t-shirt. I silently walked past and used the bathroom.

As if this night could get any more awkward.

Returning from the bathroom Trent asked me if I was ready to go. I paused for a moment and replied, "Actually, I'm not." At that point John came out of the bedroom, stood in the doorway, and politely asked me to grab him a soda from the refrigerator. What a sight! The magnificently muscled Johnny Mac standing there completely naked, with his flaccid yet still huge cock dangling halfway down his thigh. I couldn't help but laugh at Trent's reaction. You could tell he felt completely emasculated.

John suggested that Trent take Kathy back to his place for the night, but Trent sheepishly declined. From there I suggested that if Trent didn't want to take Kathy with him that was fine. I wanted to stay longer and if he didn't want to wait it out, maybe John could bring me home the next day. John then put his arms around me and began to kiss me again, interjecting "because we're not done." I squealed with delight and while kissing John back I grabbed his penis and groaned loudly. From there I dropped to my knees and greedily started sucking John's cock right there in the living room, right in front of Trent and Kathy.

Then while flicking my tongue around the head of John's penis, I looked at Trent, shrugged, and said "you're the one that wanted to swap, baby."

Before long John and I were back in the bedroom, kissing, groping, and sucking like crazed jackrabbits. He rolled me onto my back and started putting his cock in me, only to abruptly stop. "What do you want me to do?" he asked. I responded, telling him I wanted him to make love to me. John again started slowly putting his penis inside me but stopped again. "C'mon, tell me what you want me to do".

Instinctively I knew what he wanted me to say, but it was hard for me. Finally I whispered "I want you to fuck me."

And with that John started pumping away while saying "I can't hear you Michelle- you need to speak louder." He knew what I wanted: another good screwing. I sensed what he wanted, for me to be a really bad girl, and be loud enough for Trent and Kathy to hear it. But make no mistake, by the time John had me screaming "OH GOD, FUCK ME, FUCK ME, FUCK ME!!!" there wasn't a hint of phoniness to it. Once again, I was having multiple orgasms.

1-7: ELBOWS, KNEES, AND THE PALM OF ONE'S HAND

At some point John had me roll over so that I was on my stomach. He pushed my legs forward and instructed me to get on my elbows and knees. I did so, but I began to panic. I'd never even considered doing anal sex before and I was deathly afraid John would tear my insides apart with that penis. I actually felt myself shaking when I timidly asked, "Are you going to do me in the ass?"