My Best Friend's Fiance

I have been friends with Leo forever. Our parents bought houses in the same subdivision before we were born, they naturally became close friends by having children so close in age so we've been friends since the day I was born. He is a year older than me but we still were inseparable growing up. We were like brothers and over the years, we got into trouble together, got drunk, and smoked more than our fair share of joints. We each shared collections of Playboy magazines we found in our fathers' secret hiding places. We've had some fun times, laughed, fought, and had some rough patches, but through it all, we always had each other. We would do anything for each other.

Leo and I have different personalities; maybe that's why we get along so well. While Leo is more cautious and reserved, I am a risk-taking, loud, and boisterous party animal. He was always an A student while I struggled to get C's. I'm more of a big bear type of guy at 6'5" and over 250 lbs. I've had a beard on and off since I was a teen. In contrast, Leo is slender and tall by most standards at 6' but looks much shorter next to me with his slender frame. I have dark hair and brown eyes while Leo has blonde hair and blue eyes.

When we started dating women, he seemed to stick with one girl at a time, while I played the field. The more the merrier in my mind. I know there were times when Leo was envious of me but there were times when I was envious of him also. Sometimes I wished I had one girl that I could come home to rather than sleeping around. I tried being faithful to one woman but I was too easily tempted and followed my dick rather than my heart. Girls seem to like bad boys such as me and it was always difficult for me to resist an available piece of ass.

A few times, Leo asked me, "Evan, are you ever going to settle down? If you keep going like this, you're going to party yourself to an early grave or you're going to die a lonely old man."

"That may be so, buddy, but, at least I'll die with a smile on my face."

He would just shrug his shoulders. I think he knew he couldn't change me but that didn't stop him from being worried about me. Leo was my big brother trying to look out for me but I was having too much fun to listen to him or anybody else. We grew apart when he went away to college but quickly reignited our friendship when he returned home.

About two years after he graduated college, Leo met Elaine. They worked together, started flirting, then started dating. Elaine is a lovely woman in every sense of the word. She is a kind, caring, warm, and giving person with a broad smile that gives her dimples on her cheeks that immediately puts you at ease. Her hair is shoulder-length, light brown with blonde highlights, and perfectly frames her heart-shaped face. Her eyes change from hazel to light blue to dark green depending on the lighting. Elaine is a small-framed woman of above-average height with smaller breasts that seem like they could fit into a martini glass, an hourglass figure that leads to wider hips with an alluring, curvy but not fat ass. Her thighs have just the right amount of meat to them.

When Elaine first met me, it was at a barbeque at a mutual friend's house of Leo and me she said in a friendly manner, "Oh, Evan, it's nice to meet you. Leo told me all about you."

"Oh, so he told you how charming and handsome I am and that I'm a great lover?"

Elaine snickered and replied, "Oh no. He told me you were a bullshit artist and had a small penis."

A lady would rarely catch me off guard but Elaine did just that, and I was left speechless.

Elaine saw the stunned look on my face, laughed, and said, "Seriously, he told me you're an incurable flirt but you're harmless."

Leo was correct. I would always flirt with his girlfriends or every woman for that matter but he knew that I would never, ever try to fuck anyone he was dating. He tolerated my flirting with confidence that I wouldn't do anything to harm our brotherly relationship. I may have pushed his trust in me a little too far at times but he knew, in the end, that he could trust me.

Elaine and I both laughed and I replied, "He's only partially correct. I am an incurable flirt but I'm anything but harmless," giving her a devilish wink.

It was Elaine that was now speechless. She managed a slight smile while we chatted a bit before Leo called her over to introduce her to more of our friends. You could tell Leo saw something special in Elaine. As she walked away, I couldn't help but stare at her long slender legs, and thighs. She had some muscle definition in her thighs and calf muscles that led up to her gorgeous ass which wiggled as she walked in her tight jean shorts.

You know they say about a woman's ass, "A tight ass gives her more wiggle when she walks while a loose ass gives her more jiggle."

When she was about ten feet from me, she turned to look at me, catching me staring at her. Elaine gave me a sly smile then continued walking away but noticeably giving her booty an extra wiggle knowing I was watching her every step.

I was thinking, "And she called me an incurable flirt."

Throughout the rest of the afternoon and evening, I couldn't keep my eyes off of Elaine. There was something about the way her hair perfectly framed her face, her captivating personality, and her sassy confidence that set her aside from Leo's past girlfriends. She had a warm, beaming, dazzling smile that immediately charmed people and made her high cheeks more pronounced. It was impossible not to like her. Elaine's long neck led to her smallish, pert breasts that looked bigger in her tight crop-top shirt. which also served to highlight her hourglass waist and taut abdomen. Not only was Elaine beautiful and sexy but she was also intelligent and charming. Leo had found the perfect woman which left me somewhat jealous.

The more I drank that afternoon and evening, the more my eyes followed Elaine around the backyard as she socialized with our friends. It was obvious that she and Leo had some magic between them. I was thrilled for my best friend. However, that didn't stop me from undressing Elaine with my eyes. I wondered if her breasts were really that round or was it just the effects of her bra. Was her areola dime-sized, or did it fully surround the front of her breast, or somewhere in between? What did her ass look like under those tight shorts? What did those luscious cheeks feel like? Was her pussy bare or neatly trimmed? Did it taste as sweet as it looked? Was she a tigress in the bedroom or was that just what I imagined her to be? Those full lips that framed her charming smile looked like they were made to give the perfect blow job but could she suck a dick as well as I hoped? Unfortunately, I would probably never know the answers to my questions but it was fun to wonder.

Over the ensuing months, it became quite obvious that Leo and Elaine were getting more serious by the day. They were inseparable. That meant that I would socialize a lot with them with whatever girl I was dating at the time. We would drink together and pass an occasional joint around. There was some good-natured laughing, teasing, and flirting that went on but nothing serious; it was all in good fun. Anytime I saw Elaine, I always made it a point to tell her how beautiful she looked in whatever outfit she was wearing, even if it was an old shirt and sweatpants. I know she thought it was part of my normal flirtatious self but I really meant it. She looked good in whatever she was wearing and I always pictured her naked.

When you spend as much time as I did with Leo and Elaine, either watching football alone with him or double dating, it meant I caught various glimpses of her body parts. If Elaine leaned over to pour a beer into my glass, I would glance down her top at her bra encased breasts or if she were wearing a short skirt, I would possibly catch a quick peek at her panties. Even if I couldn't see her panties, I still stole glances at her long, firm legs from her perfectly manicured toes and painted nails, up her shins and past her knees to her thighs. Damn, Elaine had nice legs. I would often dream of seeing those bare legs spread wide for me as I slid my dick into her, picturing her wrapping them around my back and fucking me in return. I would never even attempt to fuck my best friend's girlfriend so I would be left to jerk off thinking of what I wanted to do to her or if I was with another woman, I'd close my eyes and fantasize that it was Elaine underneath me on the receiving end of my thrusts.

When I would be alone with Leo while at their house or out for an evening with the boys, I would always tell him how lucky he was to find a woman like Elaine. He knew what I was like more than anyone so he knew I was checking out his girlfriend every chance I got. Leo would taunt me at times also. He would tell me what a gorgeous ass she had or how much he liked her long, lean legs, or how much she liked having her titties played with. Leo was always telling me how Elaine loved to suck dick or that she was a wild woman in bed. I told him more than once that if he ever broke up with her that I'd be at her door that night trying to fuck her. It never bothered Leo knowing I had a crush on his girlfriend. I think he knew I would never act on my feelings and he also found solace in the fact that, for once, I was jealous of him. Leo had something that I couldn't have.

Elaine also knew I had a crush on her. It was pretty darn obvious from my constant flirting with her and once she got to know me better, I think she liked it. I was a hound dog who could sleep with almost any woman I wanted, except her and I think it made her feel sexy that I found her attractive. After Elaine and Leo had been together for about a year, they moved in together when they got engaged. That's when I noticed Elaine starting to flirt back with me. She was confident that I would never do anything to hurt my best friend so it was safe to tease me back.

Now that they lived together, Elaine would dress more casually around me. She was at home and dressed more comfortably than when we were out. One time I picked up Leo early on a Saturday morning to play a round of golf and Elaine was up making us coffee. She was wearing a cotton nightgown that came below her knees; it wasn't sexy at all. Well, I didn't find it sexy until she walked past the patio door with the sunlight behind her. Her nightgown became almost transparent and it looked like her silhouette glowed from the morning sun. I could clearly see her naked legs, light blue bikini panties, and her pert breasts and quarter-sized areola. I don't know if she knew I could see her nakedness underneath but her nipples got hard which only drew my attention to them. I watched her breasts bouncing freely as she moved around the kitchen while I was getting momentary flashes of her nakedness whenever she passed by the patio door.

I almost lost it when she spilled some coffee on the floor and bent down to wipe it up, giving me a clear view down her gown at her perky breasts. I didn't need the coffee to wake me up anymore. Seeing my best friend's half-naked fiance did the trick. I felt an urge to bend her over the kitchen table and pound that pussy hard but I mustered all of my self-control and watched as a silent voyeur as her body was put on display.

When Leo came into the kitchen he asked, "Are you okay buddy? You don't look so good."

"I'm fine. I'm still waking up from partying too much last night as usual."

As we grabbed our coffee in our mugs, Elaine was bent over looking for something under the sink.

Her pantied ass pressed against her cotton gown. Leo caught me looking at his fiance's ass, grinned, and said, "Are you ready?"

My best friend broke my concentration and I replied, "Um, uh, yeah. Let's get going."

There was no doubt Elaine was a sexy woman in her sweet innocent kind of way. She has that girl next door look about her. With her natural beauty, she doesn't need a lot of makeup to enhance her looks. Her attraction is in her genuineness. I think the fact that she was my best friend's fiance made her even more attractive to me. I knew she was off-limits. I always seemed to want things I couldn't have and Elaine was one of them. Even so, if I couldn't have her, I was happy that Leo found the woman of his dreams. Elaine would never be mine but I was happy for him.

I continued to flirt with Elaine whenever we were together and she was teasing me in return but in a much more subtle way. She knew I was checking her out every chance I got and seemed to be wearing tight shorts, or short skirts along with loose tops around me with greater frequency. What led me to believe she might be teasing me on purpose was the fact that whenever she would bend over in her shorts or lean over in front of me in her loose tops, she would always look up at me to catch me staring at her. Sometimes, she'd give me a modest grin, seemingly to tell me I got caught. I would give her a wink at times to acknowledge my guilt and appreciation of her cute body.

I remember one time when she was wearing a short skirt while we were drinking out on the patio, Leo went to grab us some beers and Elaine was sitting with her legs crossed. When Leo left, she began to bounce her leg while dangling her shoe from the tip of her toes. I couldn't help but to be distracted and once I began to look at her luscious, tanned legs. Elaine looked directly at me, uncrossed her legs, and parted them momentarily, exposing her white lace panties. I could plainly see the outlines of a landing strip of pubic hair. As I stared between her legs, Elaine lifted one higher than necessary and crossed it over the other, ending my little peep show.

When I raised my eyes to continue talking to Elaine, she was staring directly at me. She knew exactly what she was doing by exposing her panties to me. Elaine knew I was an easy mark and was deliberately teasing me. Even when Leo returned, Elaine would occasionally uncross her legs and cross them again or sit there with her legs parted slightly. I couldn't be as obvious in my stares with Leo sitting right there but there was no doubt she was pressing my buttons. Heck, if a woman is going to show me her panties, I'm going to look. It was a turn-on to steal surreptitious glances up her skirt.

One Sunday a couple of months later, I was watching the late-night football game with Leo, drinking beers and hanging out, nothing out of the ordinary. Elaine was wearing a pair of white running short shorts that hugged that gorgeous round ass of hers. I could see just a hint of her light pink bikini panties underneath which were more prominent if I was lucky enough to catch her bending over. I had a little buzz going from the beer and I told her how much those shorts were driving me crazy.

"Oh, these old things," Elaine said. "You're such a horndog, Evan," and she wiggled her ass at me.

I looked over at Leo and he was smiling and shaking his head. It seemed like Elaine was making it a point to show off her ass to me after that. She bent over more than a few times over the pretense of getting more chips from the bowl on the coffee table, she'd then look over her shoulder to see if I was watching. Of course, I was checking her out. I'd glance over at Leo and he noticed I was looking at his future wife's ass. When he raised his eyebrow and joined me in looking at her ass, I knew he wasn't offended.

At halftime, I went to the bathroom and then headed to the kitchen to get another beer where I saw Elaine bent over at the waist grabbing a beer from the bottom shelf. I saw her pink panties pressing against the white fabric of her shorts, perfectly framing her cushiony cheeks. I lost what little control I had left and walked up behind her, pressing my hips against her ass and fondled her cheeks. My fingers sunk into Elaine's well-cushioned ass. I had dreamt of what her cheeks would feel like and it was better than I had imagined. My fingers moved like I was kneading dough.

"Whoa," Elaine called out as she stood up quickly, then said, "Oh, I thought you were Leo."

The odd thing was she didn't object so I stood there pressed up against her ass, clutching her cheeks while she bent over again and got me a beer. Before standing up she even wiggled and pushed her ass against me. I'm sure she could feel my growing erection. When we turned around, Leo was standing in the doorway and my heart sunk. I didn't want Leo to get pissed off. I thought I fucked up big time but he simply smiled and took a beer from Elaine. We went back into the family room to finish watching the game as if nothing happened.

Elaine was sitting between me and Leo on the sofa and I couldn't take my eyes off her smooth legs that she had stretched out with her bare feet on the coffee table. My eyes kept tracing over the length of her legs from her toes to her thighs. Her shorts were so small that most of her thighs were exposed and I desperately wanted to run my hands over them. They looked so soft and tempting but I figured I already pushed my luck by fondling her ass and getting caught. I was feeling guilty for grabbing my best friend's fiance's ass and when Elaine left the room I apologized to Leo.

"Hey man, I'm, uh, sorry about what happened earlier. I came into the kitchen and when I saw Elaine bent over like that, I, uh, sort of lost control."

"That's okay, Evan. It didn't look like she minded. To be honest, when you flirt with her I think it boosts her confidence. She's probably going to fuck my brains out later."

I wasn't sure how to respond to that statement. I didn't know if he was rubbing it in that even though I had a crush on his fiance that he was the one that fucks her, almost thanking me for getting her worked up or a combination of both. I was only happy I hadn't ruined our friendship.

"I don't want you and Elaine to get pissed at me. Your friendship means too much to me."

"I appreciate that Evan. We're all friends and I know nothing would ever happen between you two. I trust Elaine and even though I know you'll fuck just about any woman that's willing, I know you'd never try and fuck her. I know it was all in good fun."

Nothing more happened that evening but I rubbed one out before I went to sleep that night thinking of having my hands around Elaine's soft, tender ass. When I talked to Leo during the week, he confirmed he and Elaine had some wild sex not only on Sunday night but on Monday and Tuesday as well. Hearing that only made me more envious of my best friend.

Maybe it was Leo's way of telling me, "you can drool over Elaine all you want, even grab her ass but she's all mine."

Elaine didn't always tease me when I saw her. Sometimes we would be at a party or with a larger gathering of people and nothing would happen. It seemed that she felt more comfortable within the confines of her home when it was just the three of us. I was over at their house early on another Saturday. I forgot why I was even there but Leo and I were in the kitchen having coffee and I could hear the shower going. I was chatting with Leo and suddenly Elaine came into the kitchen with a towel wrapped around her. I couldn't help but stare at her bare legs. I'd seen more of her body before but the thing that attracted my attention was the fact that I knew she was naked underneath. Fuck, I found that so sexy.

"Oh, hi Evan. I didn't know you were here. Sorry about the way I'm dressed. I just came to get a cup of coffee."

"You don't have to apologize to me, Elaine. I kind of like that look on you."

"You're such a perv, Evan."

"Like you're surprised by that fact, eh?"

Elaine giggled as she poured herself some coffee, then turned to face us as she took a sip. I was staring at her wishing that towel would come loose. I saw where it was tucked in across her upper chest and I was trying to use mental powers to make it come undone. Just then, Elaine raised her arms to take another sip of coffee and the towel slid down her body leaving her naked in front of us. My mouth hung open as my eyes widened.